Bulgarian-Ottoman Wars
Encyclopedia
The Bulgarian-Ottoman wars were fought between the disintegrating Bulgarian Empire
Second Bulgarian Empire
The Second Bulgarian Empire was a medieval Bulgarian state which existed between 1185 and 1396 . A successor of the First Bulgarian Empire, it reached the peak of its power under Kaloyan and Ivan Asen II before gradually being conquered by the Ottomans in the late 14th-early 15th century...

 and the new emerging Turkic
Turkic peoples
The Turkic peoples are peoples residing in northern, central and western Asia, southern Siberia and northwestern China and parts of eastern Europe. They speak languages belonging to the Turkic language family. They share, to varying degrees, certain cultural traits and historical backgrounds...

 power, the Ottoman Turks
Ottoman Turks
The Ottoman Turks were the Turkish-speaking population of the Ottoman Empire who formed the base of the state's military and ruling classes. Reliable information about the early history of Ottoman Turks is scarce, but they take their Turkish name, Osmanlı , from the house of Osman I The Ottoman...

 in the second half the 14th century and the beginning of the 15th century. The war ended with the collapse of the once powerful Bulgarian Empire in 1422. The Bulgarians reestablished their state after almost five centuries of Ottoman domination in 1878. As a result of the wars the Ottoman Empire greatly expanded its territory on the Balkan peninsula, stretching from the river Danube
Danube
The Danube is a river in the Central Europe and the Europe's second longest river after the Volga. It is classified as an international waterway....

 to the Aegean Sea
Aegean Sea
The Aegean Sea[p] is an elongated embayment of the Mediterranean Sea located between the southern Balkan and Anatolian peninsulas, i.e., between the mainlands of Greece and Turkey. In the north, it is connected to the Marmara Sea and Black Sea by the Dardanelles and Bosporus...

. In Bulgaria that period is usually described as the struggle of the Bulgarian people against the Ottoman army.

The situation in the Balkans on the eve of the Ottoman invasion

From the 13th century, in the two main Balkan powers Byzantium
Byzantine Empire
The Byzantine Empire was the Eastern Roman Empire during the periods of Late Antiquity and the Middle Ages, centred on the capital of Constantinople. Known simply as the Roman Empire or Romania to its inhabitants and neighbours, the Empire was the direct continuation of the Ancient Roman State...

 and Bulgaria
Bulgarian Empire
Bulgarian Empire is a term used to describe two periods in the medieval history of Bulgaria, during which it acted as a key regional power in Europe in general and in Southeastern Europe in particular, rivalling Byzantium...

 which used to be strongly centralized began the process of decentralization as the local feudal lords grew stronger and more independent from the Emperors in Constantinople
Constantinople
Constantinople was the capital of the Roman, Eastern Roman, Byzantine, Latin, and Ottoman Empires. Throughout most of the Middle Ages, Constantinople was Europe's largest and wealthiest city.-Names:...

 and Tarnovo which weakened their military and economic power. These processes grew even stronger in the 14th century with numerous nobles being only nominally submitted to the central government. In Bulgaria the strong house of Shishman ruled over the Vidin Province to the west, while to the east the noble Balik was trying to get more independence from Tarnovo.

While the two Empires were facing enormous internal difficulties, the Serbs
Serbs
The Serbs are a South Slavic ethnic group of the Balkans and southern Central Europe. Serbs are located mainly in Serbia, Montenegro and Bosnia and Herzegovina, and form a sizable minority in Croatia, the Republic of Macedonia and Slovenia. Likewise, Serbs are an officially recognized minority in...

 took the favourable opportunity to expand their kingdom. During the civil war in Byzantium in 1320s and 1330s, they managed to conquer most of the Bulgarian
Bulgarians
The Bulgarians are a South Slavic nation and ethnic group native to Bulgaria and neighbouring regions. Emigration has resulted in immigrant communities in a number of other countries.-History and ethnogenesis:...

 populated Macedonia
Macedonia (region)
Macedonia is a geographical and historical region of the Balkan peninsula in southeastern Europe. Its boundaries have changed considerably over time, but nowadays the region is considered to include parts of five Balkan countries: Greece, the Republic of Macedonia, Bulgaria, Albania, Serbia, as...

, which was then held by the Byzantines. In 1330 the Serbs defeated the Bulgarian Emperor Michail Shishman
Michael Shishman of Bulgaria
Michael Asen III ), ruled as emperor of Bulgaria from 1323 to 1330. The exact year of his birth is unknown but it was between 1280 and 1292. He was the founder of the last ruling dynasty of the Second Bulgarian Empire, the Shishman dynasty...

 at Velbazhd and emerged as the most powerful state in the region and in 1346 their king Stefan Uroš IV Dušan
Stefan Uroš IV Dušan of Serbia
Stephen Uroš IV Dušan the Mighty , was the King of Serbia and Emperor of the Serbs and Greeks until his death on 20 December 1355. Dušan managed to conquer a large part of Southeast Europe, becoming one of the most powerful monarchs in his time...

 received Imperial title with the blessing of the Bulgarian Emperor Ivan Alexander
Ivan Alexander of Bulgaria
Ivan Alexander , also known as John Alexander, ruled as Emperor of Bulgaria from 1331 to 1371, during the Second Bulgarian Empire. The date of his birth is unknown. He died on February 17, 1371. The long reign of Ivan Alexander is considered a transitional period in Bulgarian medieval history...

. However, after his death in 1355, his large Empire disintegrated into numerous completely independent states. In the same time in Bulgaria Ivan Alexander gave the rule of Vidin to his first son, Ivan Sratsimir in 1356 and in Dobrudzha ruled despot Dobrotitsa
Dobrotitsa
Dobrotitsa was a Bulgarian noble, ruler of the de facto independent Principality of Karvuna and the Kaliakra fortress from 1354 to 1379–1386....

 who was nominally subjected to him. In 1341-1347 the Byzantine Empire was shaken in a bloody civil war between John V Palaiologos
John V Palaiologos
John V Palaiologos was a Byzantine emperor, who succeeded his father in 1341, at age nine.-Biography:...

 and John VI Kantakouzenos
John VI Kantakouzenos
John VI Kantakouzenos or Cantacuzenus was the Byzantine emperor from 1347 to 1354.-Early life:Born in Constantinople, John Kantakouzenos was the son of a Michael Kantakouzenos, governor of the Morea. Through his mother Theodora Palaiologina Angelina, he was a descendant of the reigning house of...

.

Towards the middle of the century the Balkans were tens of small states constantly in war or plotting against each other with not a single strong country with a large army. In addition to the mainly Orthodox
Eastern Orthodox Church
The Orthodox Church, officially called the Orthodox Catholic Church and commonly referred to as the Eastern Orthodox Church, is the second largest Christian denomination in the world, with an estimated 300 million adherents mainly in the countries of Belarus, Bulgaria, Cyprus, Georgia, Greece,...

 countries such as Bulgaria, Byzantium and Serbia, there were a number of Catholic
Catholic
The word catholic comes from the Greek phrase , meaning "on the whole," "according to the whole" or "in general", and is a combination of the Greek words meaning "about" and meaning "whole"...

 possessions to the west and south held by Venice
Venice
Venice is a city in northern Italy which is renowned for the beauty of its setting, its architecture and its artworks. It is the capital of the Veneto region...

, Genova
Génova
Génova may refer to:* Spanish spelling of the city of Genoa, Italy* Génova, Quindío, a municipality in the department of Quindío, Colombia* Génova, Quetzaltenango, a municipality in the department of Quetzaltenango, Guatemala...

 and the Kingdom of Hungary
Kingdom of Hungary
The Kingdom of Hungary comprised present-day Hungary, Slovakia and Croatia , Transylvania , Carpatho Ruthenia , Vojvodina , Burgenland , and other smaller territories surrounding present-day Hungary's borders...

 as well as Kingdom of Bosnia whose Bosnian Church
Bosnian Church
The Bosnian Church is historically thought to be an indigenous branch of the Bogomils that existed in Bosnia during the Middle Ages. Adherents of the church called themselves simply Krstjani...

 (closely related to the Bogomils) was considered heretic by both Orthodox and Catholics. The religious diversity was another source for the constant tensions in the region.

Military actions during the reign of Ivan Alexander

During the civil war in Byzantium both Palaiologos and Kantakouzenos were trying to find external allies and used foreign mercenaries. The Bulgarian Emperor supported the first opponent whose stronghold was Constantinople. John Kantakouzenos on the other hand regularly hired Ottoman Turk mercenaries from Asia Minor
Asia Minor
Asia Minor is a geographical location at the westernmost protrusion of Asia, also called Anatolia, and corresponds to the western two thirds of the Asian part of Turkey...

 whose bands soon became a common thing in Thrace
Thrace
Thrace is a historical and geographic area in southeast Europe. As a geographical concept, Thrace designates a region bounded by the Balkan Mountains on the north, Rhodope Mountains and the Aegean Sea on the south, and by the Black Sea and the Sea of Marmara on the east...

. Despite being their allies, the Byzantines could not fully control them and they brought the region into ruins and launched regular attacks on Bulgarian territory to plunder the villages.
In 1344 the independent Bulgarian ruler of the Rhodope and Aegean
Aegean Sea (theme)
The Theme of the Aegean Sea was a Byzantine province in the northern Aegean Sea, established in the mid-9th century. As one of the Byzantine Empire's three dedicated naval themes , it served chiefly to provide ships and troops for the Byzantine navy, but also served as a civil administrative...

 regions Momchil
Momchil
Momchil was a 14th-century Bulgarian brigand and local ruler. Initially a member of a bandit gang in the borderlands of Bulgaria, Byzantium and Serbia, Momchil was recruited by the Byzantines as a mercenary...

 whose army grew to 2,000 men took an important role in the Byzantine civil war. At first he supported John Kantakouzenos but from the spring of 1344 he reneged on him due to the atrocities of his Ottoman allies. In June he defeated the Ottoman fleet near the Portogalos bay. At night he sent boats which burned the anchored ships of the enemy. Soon after this success he defeated the army of Kantakouzenos at Mosinopol.

He was among the first local rulers who realized the threat of the Ottomans. Momchil pleaded both the Emperors of Bulgaria and Byzantium for help but received none. Even though he continued the resistance in the eastern part of the Rhodope mountains. In May 1345 the Turks led by Uner beg marched from Asia Minor to the Balkan Peninsula and made a devastating raid on Bulgarian territory driving away many people and cattle. Soon after that, on 7 July 1345 the Bulgarian forces were defeated in the battle of Peritor
Battle of Peritor
The Battle of Peritheorion on 7 July 1345 between the forces of Momchil, the quasi-independent ruler of Rhodope, and an allied Byzantine-Turkish force headed by John VI Kantakouzenos and Umur Bey of Aydin...

 near Momchil's seat Xanthi
Xanthi
Xanthi ; is a city in Thrace, northeastern Greece. It is the capital of the Xanthi peripheral unit of the periphery of East Macedonia and Thrace.-History:...

 by superior Ottoman forces under Uner beg and Momchil perished in the battle.

During the civil wars in the Byzantine Empire Ivan Alexander regained the control of several towns in Thrace and the Rhodopes but his frequent interference in the internal affairs of Byzantium hampered any closer relations between the two counties although they were in peace from 1332. In 1352 new Turkish forces invaded Bulgaria, devastated its southern areas and returned with huge spoils. Aitos, Diampol and Plovdiv
Plovdiv
Plovdiv is the second-largest city in Bulgaria after Sofia with a population of 338,153 inhabitants according to Census 2011. Plovdiv's history spans some 6,000 years, with traces of a Neolithic settlement dating to roughly 4000 BC; it is one of the oldest cities in Europe...

 suffered most. In the same year the Ottomans seized their first fortress on the Balkans, Tsimpe in the Galipoli peninsula and soon set firm foot in Europe. Between 1352 and 1354 they ravaged the lands around Yambol
Yambol
Yambol is a city in southeastern Bulgaria, an administrative centre of Yambol Province. It lies on both banks of the Tundzha river in the historical region of Thrace. As of February 2011, the town has a population of 72,843 inhabitants. It is occasionally spelt 'Jambol'.The administrative centres...

 and Plovdiv
Plovdiv
Plovdiv is the second-largest city in Bulgaria after Sofia with a population of 338,153 inhabitants according to Census 2011. Plovdiv's history spans some 6,000 years, with traces of a Neolithic settlement dating to roughly 4000 BC; it is one of the oldest cities in Europe...

 as well as the lower reaches of the Maritsa
Maritsa
The Maritsa or Evros , ) is, with a length of 480 km, the longest river that runs solely in the interior of the Balkans. It has its origin in the Rila Mountains in Western Bulgaria, flowing southeast between the Balkan and Rhodope Mountains, past Plovdiv and Parvomay to Edirne, Turkey...

 and Tundzha
Tundzha
The Tundzha is a river in Bulgaria and Turkey and the most significant tributary of the Maritsa, emptying into it on Turkish territory near Edirne....

 rivers.

In 1355 the Ottomans launched a campaign in the direction of Sofia
Sofia
Sofia is the capital and largest city of Bulgaria and the 12th largest city in the European Union with a population of 1.27 million people. It is located in western Bulgaria, at the foot of Mount Vitosha and approximately at the centre of the Balkan Peninsula.Prehistoric settlements were excavated...

 and were engaged by a Bulgarian army under Ivan Alexander's eldest son and heir Michael Asen in the vicinity of the city, probably around Ihtiman
Battle of Ihtiman
The Battle of Ihtiman occurred in 1355 between Bulgarians and Ottomans and resulted in Ottoman victory. The exact location is not known, but in an anonymous Bulgarian chronicle, it is mentioned that the armies of Michail Asen engaged the invading forces before they could reach Sofia.- Origins of...

. In the following battle the Turks prevailed. Both sides suffered heavy casualties including the young Micheal Asen but eventually the Turks did not reach Sofia.

The unexecuted alliance

The defeat raised serious alert not only in Tarnovo but also in Constantinople and John Kantakouzenos was forced to abdicate. Thus one of the main perpetrators of the Ottoman invasion was removed from the political scene. Faced with that threat, Bulgaria and Byzantium made an attempt for rapprochement. In 1355 the daughter of the Bulgarian Emperor, Keratsa married the son of the new Byzantine Emperor John V, the infant Andrinokos. The new relations between the houses of Tarnovo and Constantinople should have been harmful to the invaders but despite the anticipation the agreement did not pay off.
In that period the Bulgarian and Byzantine Empires were once again the major political power on the peninsula and the only countries which were able to stop the penetration of the Ottoman Turks and seriously resist them. After the death of Stefan Dushan on 20 December 1355 Serbia lost its political influence and his large but ethnically diverse country split into many states. Between 1354 and 1364 the Turks became masters of Thrace
Thrace
Thrace is a historical and geographic area in southeast Europe. As a geographical concept, Thrace designates a region bounded by the Balkan Mountains on the north, Rhodope Mountains and the Aegean Sea on the south, and by the Black Sea and the Sea of Marmara on the east...

 and a number of important castles and towns fell under their attacks including Plovdiv and Stara Zagora
Stara Zagora
Stara Zagora is the sixth largest city in Bulgaria, and a nationally important economic center. Located in Southern Bulgaria, it is the administrative capital of the homonymous Stara Zagora Province...

. From the end of the 1350s some Ottoman companies even reached the surroundings of the capital and the Emperor took precautions to repair the decayed walls of the city. It is known from the records of the Ottoman chronicler Seadeddin and other chronicles that the Ottoman advance between 1359 and 1364 involved enormous destruction and total depopulation of certain areas. Many cities were devastated (Plovdiv, Stara Zagora, Sliven
Sliven
Sliven is the eighth-largest city in Bulgaria and the administrative and industrial centre of Sliven Province and municipality. It is a relatively large town with 89,848 inhabitants, as of February 2011....

) while others such as Venets and Sotirgrad disappeared forever. The devastation was accompanied by mass slaughter or deportation of population to Asia Minor.

Not only was there a total lack of coordination between the two Empires but they also quarreled for the Black Sea
Black Sea
The Black Sea is bounded by Europe, Anatolia and the Caucasus and is ultimately connected to the Atlantic Ocean via the Mediterranean and the Aegean seas and various straits. The Bosphorus strait connects it to the Sea of Marmara, and the strait of the Dardanelles connects that sea to the Aegean...

 ports of Nessebar and Pomorie
Pomorie
Pomorie is a town and seaside resort in southeastern Bulgaria, located on a narrow rocky peninsula in Burgas Bay on the southern Bulgarian Black Sea Coast. It is situated in Burgas Province, 20 km away from the city of Burgas and 18 km from the Sunny Beach resort. The ultrasaline lagoon...

 which the Bulgarians successfully defended in 1364. The war brought nothing to the two parties involved but completely ruined the relation between the two states.

The last years of Ivan Alexander

Apart from the threat from the south, Bulgaria had other problems: in 1365 the Hungarian
Kingdom of Hungary
The Kingdom of Hungary comprised present-day Hungary, Slovakia and Croatia , Transylvania , Carpatho Ruthenia , Vojvodina , Burgenland , and other smaller territories surrounding present-day Hungary's borders...

 King Louis I invaded north-western Bulgaria, seized the large fortress Vidin and captured the eldest surviving son of the Emperor, Ivan Sratsimir
Ivan Sratsimir of Bulgaria
Ivan Sratsimir or Ivan Stratsimir was emperor of Bulgaria in Vidin from 1356 to 1396. He was born in 1324 or 1325, and he died in or after 1397. Despite being the eldest surviving son of Ivan Alexander, Ivan Sratsimir was disinherited in favour of his half-brother Ivan Shishman and proclaimed...

. In futile attempts to reconquer Vidin Ivan Alexander even used Ottoman mercenaries. However, in the summer of 1369 the Bulgarian Emperor restored his authorities over the Vidin Province with the help of the Wallachian voivoda Vladislav I
Vladislav I of Wallachia
Vladislav I of the Basarab dynasty, also known as Vlaicu-Vodă, was a ruler of the principality of Wallachia . He was a vassal of the Bulgarian Emperor Ivan Alexander. In 1369 Vladislav I subdued Vidin and recognised Louis I of Hungary as his overlord in return for Severin, Amlaş, and Făgăraş...

 but that proved to be his last success - on 17 February 1371 he died.

After Ivan Alexander's death the Bulgarian lands were divided in several independent states. Most of the area with centre Tarnovo came under his third son Ivan Shishman
Ivan Shishman of Bulgaria
Ivan Shishman ruled as emperor of Bulgaria in Tarnovo from 1371 to 3 July 1395. The authority of Ivan Shishman was limited to the central parts of the Bulgarian Empire. His indecisive and inconsistent policy did little to prevent the fall of his country under Ottoman rule. In 1393 the Ottoman...

, in Vidin ruled his eldest son Ivan Sratsimir
Ivan Sratsimir of Bulgaria
Ivan Sratsimir or Ivan Stratsimir was emperor of Bulgaria in Vidin from 1356 to 1396. He was born in 1324 or 1325, and he died in or after 1397. Despite being the eldest surviving son of Ivan Alexander, Ivan Sratsimir was disinherited in favour of his half-brother Ivan Shishman and proclaimed...

, despot Dobrotitsa
Dobrotitsa
Dobrotitsa was a Bulgarian noble, ruler of the de facto independent Principality of Karvuna and the Kaliakra fortress from 1354 to 1379–1386....

 held Dodrudzha and Macedonia
Macedonia (region)
Macedonia is a geographical and historical region of the Balkan peninsula in southeastern Europe. Its boundaries have changed considerably over time, but nowadays the region is considered to include parts of five Balkan countries: Greece, the Republic of Macedonia, Bulgaria, Albania, Serbia, as...

 was divided in several feudal feudal states ruled by Serb nobles.

The battle of Chernomen and consequences

In 1371 two feudal lords in Macedonia organised a campaign against the Turks. The Serbian king of Prilep
Prilep
Prilep is the fourth largest city in the Republic of Macedonia. It has a population of 66,246 citizens. Prilep is known as "the city under Marko's Towers" because of its proximity to the towers of Prince Marko.-Name:...

 Vukashin
Vukašin Mrnjavcevic
Vukašin Mrnjavčević was a Serbian ruler in modern-day central and northwestern Macedonia, who ruled from 1365 to 1371. According to 17th-century Ragusan historian Mavro Orbin, his father was a minor noble named Mrnjava from Zachlumia, whose sons Vukašin and Uglješa were born in Livno in western...

 and the despot of Ser
Serres
Serres is a city in Greece, seat of the Serres prefecture.Serres may also refer to:Places:* Serres, Germany, a part of Wiernsheim in Baden-WürttembergIn France:* Serres, Aude in the Aude département...

 Uglesha
Jovan Ugljesa
Jovan Uglješa Mrnjavčević was a 14th-century Serbian noble and brother of Serbian ruler Vukašin Mrnjavčević.-Life:Uglješa was the son of Mrnjava, a treasurer of Helen of Anjou, the queen consort of Stephen Uroš I of Serbia....

 who were brothers gathered a large Christian
Christian
A Christian is a person who adheres to Christianity, an Abrahamic, monotheistic religion based on the life and teachings of Jesus of Nazareth as recorded in the Canonical gospels and the letters of the New Testament...

 army to stop the Muslim invaders. Uglesha whose lands bordered with the Ottomans to the east had realized that if they were not stopped soon they would conquer the whole region and called rest of Serbia and some Bulgars for help but both states could not send troops. The army of the two brothers who were themselves Serbs but ruled over mixed Serbian-Greek-Bulgarian-populated lands set of to the east with 70,000 (according to other sources 20,000) Serbian-Bulgarian army. When they reached the village of Chernomen in the lower course of the Maritsa
Maritsa
The Maritsa or Evros , ) is, with a length of 480 km, the longest river that runs solely in the interior of the Balkans. It has its origin in the Rila Mountains in Western Bulgaria, flowing southeast between the Balkan and Rhodope Mountains, past Plovdiv and Parvomay to Edirne, Turkey...

 river their camp was attacked at night on 26 September by a considerably smaller enemy force under Lala Shahin Pasha
Lala Shahin Pasha
Lala Shahin Pasha was the first Beylerbey of Rumelia. He was one of commanders in Battle of Maritsa and the leader of the Battle of Bileća ....

 and allies were routed. Valkashin and Uglesha along with most of the army perished.

Immediately after the battle the armies of Murad I
Murad I
Murad I was the Sultan of the Ottoman Empire, from 1361 to 1389...

 headed towards Bulgaria and forced the young Emperor Ivan Shishman to pull back to the north of the Stara planina and overran northern Thrace. Many castles fell after prolonged sieges. The town of Diampol fought against the hordes under Timurtash for months but after the shortage of food the population was forced to surrender. During the fights in the southern slopes of Stara Planina one of Ivan Shishman's voivods, Shishkin perished. Soon the Ottomans seized the Rhodopes, Kostenets
Kostenets
Kostenets is a village in the Sofia Province southwestern Bulgaria, located in the Kostenets Municipality . As of the 2000 census, the village had a total population of 4,201...

, Ihtiman
Ihtiman
Ihtiman is a town in western Bulgaria, part of Sofia Province. It is located in the Ihtimanska Sredna Gora mountains and lies in a valley 48 km from Sofia and 95 km from Plovdiv, close to Trakiya motorway....

 and Samokov
Samokov
Samokov is a town in Sofia Province in the southwest of Bulgaria. It is situated in a kettle between the mountains Rila and Vitosha, 55 kilometres from the capital Sofia...

, nearly reaching the Sofia Valley
Sofia Valley
The Sofia Valley is a valley in central western Bulgaria, bordering Stara Planina to the northeast, the Viskyar, Lyulin, Vitosha and Lozen mountains to the southwest, the Vakarel Mountain to the southeast and the low Slivnitsa Heights to the northwest....

. After a bloody siege they captured Bitola
Bitola
Bitola is a city in the southwestern part of the Republic of Macedonia. The city is an administrative, cultural, industrial, commercial, and educational centre. It is located in the southern part of the Pelagonia valley, surrounded by the Baba and Nidže mountains, 14 km north of the...

 in the south-western Bulgarian lands. In 1373 Ivan Shishman had to negotiate for peace. The peace treaty was humiliating: the Bulgarian ruler became an Ottoman vassal and had to give his sister Kera Tamara
Kera Tamara
Kera Tamara was the daughter of the Bulgarian Emperor Ivan Alexander and his second wife Sarah-Theodora. Kera Tamara was a sister of Ivan Shishman and Ivan Sratsimir. She was born in the 1340s and originates from the Shishman dynasty....

 for Murad's wife. As a compensation, the Ottomans returned some of the conquered areas including Ihtiman and Samokov.

Between 1371 and 1373 the Ottomans emerged as a considerable power which every Balkan ruler had to take into an account. They ruled over the whole of Thrace and seized the lands of Uglesha in western Macedonia. The son of Valkashin Marko
Prince Marko
Marko Mrnjavčević was de jure the Serbian king from 1371 to 1395, while de facto he ruled only over a territory in western Macedonia centered on the town of Prilep...

 and Ivan Shishman became their vassals.

The fall of the Rhodopes

During the same period (1371–1373) the invaders took control of the Rhodopes, a mountain studded with strong and well-guarded fortresses. The Turks rushed in from the northern slopes of the mountains. After a fierce resistance fell the Rakovitsa fortress (now in ruins). It was besieged by the forces of Daud pasha and the defense was led by the voivoda Kurt. After futile attempts to capture the castle with force the Turk agreed to negotiations and the Bulgarians surrendered and kept their property.

The Ottomans fought bloody battles to take over one of the major castles in the Rhodopes, Tsepina
Tsepina
Tsepina was a castle and town in the western Rhodope mountains, southern Bulgaria, now in ruins. It is located at 6 km from the Dorkovo village in the north-eastern part of the Chepinska valley....

. For 9 months its population repulsed the enemy attacks but eventually surrendered in return for their lives and property after the Turks under Daud pasha cut off the water-conduit. In the same manner was taken Stanimaka (Asenovgrad
Asenovgrad
Asenovgrad is a town in central southern Bulgaria, part of Plovdiv Province.-History:Asenovgrad was founded by the Thracians as Stenímachos around 300–400 BC. In 72 BC the city was captured by the troops of the Roman Empire as part of the Roman expansion towards the Black Sea. After a long period...

). After a bitter siege fell the fortress Batkun on the northern slopes of the Rhodopes. Its commander Georgi was killed along his men in the final assault.

The Ottomans faced a stubborn resistance in the interior of the Rhodope massif. The central areas were invaded by two armies commanded by Dzhedit pasha and Ibrahim pasha. Dzhedit pasha advanced on the road Stanimaka - Bachkovo Monastery
Bachkovo Monastery
The Bachkovo Monastery , archaically the Petritsoni Monastery or Monastery of the Mother of God Petritzonitissa in Bulgaria is an important monument of Christian architecture and one of the largest and oldest Eastern Orthodox monasteries in Europe...

 along the valley of the Chepelarska river, and Ibrahim pasha set off from Plovdiv via Parvenets and then through the valley of the Vacha River
Vacha River
The Vacha is a river in south Bulgaria, one of the main right tributaries of the Maritsa. It is 105 km long and is formed by the confluence of the Shirokolashka reka and the Byunovska reka. The river passes through Krichim Dam and Vacha Dam that secure drinking water for Plovdiv and its plains...

. Fighting occurred at the fortified settlements or locations Zarenitsa, Zagrad, Gradishte, Chiltepe and Karakulas (location along the valley of the Vacha), Imaretdere and Momina Voda (heights close to Ardino
Ardino
Ardino is a town in Southern Bulgaria, in the Rhodope Mountains. It is located in Kurdzhali oblast and is close to the town of Madan.It is famous for its textile industry. It has a machine-building factory and a tobacco manufacturing industry. Tourist attractions include the Eagle rocks and the...

) and others. Especially fierce was the engagement at Momina Voda where one of the prominent Ottoman leaders Sarǎ Baba was killed. A bloody battle also occurred at Karakulas where another Ottoman chief - Enihan Baba perished.

Fall of Sofia

While Ivan Shishman was desperately trying to resist against the strong Ottoman pressure, his brother Ivan Sratsimir not only withheld reinforcements or help but tried to make use of the difficulties which his brother faced to expand his domains over certain areas of the Tarnovo Tsardom. As Shishman's attention was pointed to the south, Ivan Sratsimir took control of the important city of Sofia
Sofia
Sofia is the capital and largest city of Bulgaria and the 12th largest city in the European Union with a population of 1.27 million people. It is located in western Bulgaria, at the foot of Mount Vitosha and approximately at the centre of the Balkan Peninsula.Prehistoric settlements were excavated...

 which was disputed between the two brothers. However by 1373 the city was again in the Tarnovo Tsardom and it is possible that there might have been armed conflict between the two Bulgarian states. Despot Dobrotitsa also did not give any support to the Emperor in Tarnovo. He was in conflict with Genova
Génova
Génova may refer to:* Spanish spelling of the city of Genoa, Italy* Génova, Quindío, a municipality in the department of Quindío, Colombia* Génova, Quetzaltenango, a municipality in the department of Quetzaltenango, Guatemala...

 and was involved in the internal affairs of the Trapezund Empire
Empire of Trebizond
The Empire of Trebizond, founded in April 1204, was one of three Byzantine successor states of the Byzantine Empire. However, the creation of the Empire of Trebizond was not directly related to the capture of Constantinople by the Fourth Crusade, rather it had broken away from the Byzantine Empire...

 trying to put on its throne his son-in-law.

After the temporary hush which followed after 1373, in 1380 the Ottomans again started hostilities. With a large army Sultan Murad headed towards the south-western regions of the Tarnovo Tsardom which main objective to seize its center Sofia. After a bloody clashes in the Zlatitsa
Zlatitsa
Zlatitsa is a town in southern Bulgaria located in the Zlatitsa-Pirdop valley, between Stara Planina to the north and Sredna Gora to the south at 680 meters above the sea level. It is situated immediately south in the lap of the Zlatitsa -Teteven Mountain...

 valley the Turks moved on to Sofia and besieged it. The city which was commanded by ban Yanuka
Yanuka
Ban Yanuka , defender of Sofia from Ottoman Turks in the late 14th century was the manager/deputy of the Tsar Ivan Shishman in Sredets...

 repulsed all the attacks of the superior Ottoman forces under Lala Shahin
Lala Shahin Pasha
Lala Shahin Pasha was the first Beylerbey of Rumelia. He was one of commanders in Battle of Maritsa and the leader of the Battle of Bileća ....

. The later could not continue the siege and was forced to pull back to Odrin where he reported his failure to the Sultan. While he was absent the Turks managed to infiltrate Sofia and one Muslim Bulgarian captured ban Yanuke while hunting and sent him to Lala Shahin who was in Plovdiv at that time. From there the Bulgarian commander was sent back to Sofia and when the defenders saw their captured leader they surrendered the city
Siege of Sofia
The Siege of Sofia took place in 1382 or 1385 during the course of the Bulgarian-Ottoman Wars. Unable to defend his country from the Ottomans, in 1373 the Bulgarian emperor Ivan Shishman agreed to become an Ottoman vassal and to marry his sister Kera Tamara to their sultan Murad I, while the...

 to the Ottomans (1382).

The Ottomans installed a strong garrison and brought Muslim settlers from Asia Minor. On the following year fell Serres
Serres
Serres is a city in Greece, seat of the Serres prefecture.Serres may also refer to:Places:* Serres, Germany, a part of Wiernsheim in Baden-WürttembergIn France:* Serres, Aude in the Aude département...

 The new Ottoman success did not bring together Ivan Shishman and Ivan Sratsimir. Between 1384 and 1386 waged a war between Bulgaria and Wallachia
Wallachia
Wallachia or Walachia is a historical and geographical region of Romania. It is situated north of the Danube and south of the Southern Carpathians...

, the Vlachs
Vlachs
Vlach is a blanket term covering several modern Latin peoples descending from the Latinised population in Central, Eastern and Southeastern Europe. English variations on the name include: Walla, Wlachs, Wallachs, Vlahs, Olahs or Ulahs...

 seized several settlements along the Danube
Danube
The Danube is a river in the Central Europe and the Europe's second longest river after the Volga. It is classified as an international waterway....

 but were later defeated and their voivoda Dan I
Dan I of Wallachia
Dan I was a voivode of the principality of Wallachia . During the war with Bulgaria he perished in battle against the troops of Tsar Ivan Shishman...

 was killed. Ivan Sratsimir took part in the actions as an ally of the Vlachs which proved the total lack of coordination between the Bulgarian states and deepened the mistrust between the two brothers.

After they secured the possession of the area around Sofia, the Ottomans continued their march to the north-west. The main objective of Murad was to break the ties between Bulgaria and Serbia because despite Ivan Shishman was his vassal, Murad did not trust him and knew that the Bulgarian ruler was waiting for an appropriate opportunity to renege. In 1386 the Turks seized Pirot
Pirot
Pirot is a town and municipality located in south-eastern Serbia. According to 2011 census, the town has a total population of 38,432, while the population of the municipality is 57,911...

 and Niš
Niš
Niš is the largest city of southern Serbia and third-largest city in Serbia . According to the data from 2011, the city of Niš has a population of 177,972 inhabitants, while the city municipality has a population of 257,867. The city covers an area of about 597 km2, including the urban area,...

 after bitter fights killing and enslaving many Bulgarians.

The campaign of 1388

The advance of the Ottomans in the central parts of the Balkan peninsula caused serious anxiety not only for Ivan Shishman but also in Serbia and Bosnia
Bosnia (region)
Bosnia is a eponomous region of Bosnia and Herzegovina. It lies mainly in the Dinaric Alps, ranging to the southern borders of the Pannonian plain, with the rivers Sava and Drina marking its northern and eastern borders. The other eponomous region, the southern, other half of the country is...

. The Serbia
Serbia
Serbia , officially the Republic of Serbia , is a landlocked country located at the crossroads of Central and Southeast Europe, covering the southern part of the Carpathian basin and the central part of the Balkans...

n Prince Lazar
Lazar of Serbia
Lazar Hrebeljanović , was a medieval nobleman that emerged as the most powerful Serbian ruler after the death of the previous, childless, Emperor Uroš the Weak, which resulted in years of instability in the Serbian realm. As Stefan Lazar, he was Prince of Serbia from 1371 to 1389, ruling what is...

 and the Bosnian King Tvardko
Tvrtko I of Bosnia
Stjepan Tvrtko I was a ruler of medieval Bosnia. He ruled in 1353–1366 and again in 1367–1377 as Ban and in 1377–1391 as the first Bosnian King....

 organized an anti-Ottoman coalition and the Bulgarian Emperor joined them but was unable to send troops. In 1387 the united forces of Bosnians
Bosnians
Bosnians are people who reside in, or come from, Bosnia and Herzegovina. By the modern state definition a Bosnian can be anyone who holds citizenship of the state. This includes, but is not limited to, members of the constituent ethnic groups of Bosnia and Herzegovina: Bosniaks, Bosnian Serbs and...

 and Serbs
Serbs
The Serbs are a South Slavic ethnic group of the Balkans and southern Central Europe. Serbs are located mainly in Serbia, Montenegro and Bosnia and Herzegovina, and form a sizable minority in Croatia, the Republic of Macedonia and Slovenia. Likewise, Serbs are an officially recognized minority in...

 defeated the Turk in the battle of Plocnik
Battle of Plocnik
The Battle of Pločnik was fought in 1386 , at the village of Pločnik, near Prokuplje in today's southeastern Serbia, between the Serbian forces of prince Lazar Hrebeljanović and the invading Ottoman Turks of sultan Murad I.It was the second clash between the Ottomans and forces commanded by Lazar,...

.

However, while the Christian states did not make any attampt to use the victory, the Turks' reaction was swift. In 1388 a 30,000 strong army commanded by Ali Pasha
Çandarli Ali Pasa
Çandarlı Ali Paşa was the grand vizier of the Ottoman Empire from 1387 until 1406, under Sultans Bayezid I and, during the Ottoman Interregnum, Süleyman Çelebi. He was the son of Çandarlı Kara Halil Hayreddin Pasha and the brother of Çandarlı Ibrahim Pasha...

 passed through the eastern Balkan mountains
Balkan Mountains
The Balkan mountain range is a mountain range in the eastern part of the Balkan Peninsula. The Balkan range runs 560 km from the Vrashka Chuka Peak on the border between Bulgaria and eastern Serbia eastward through central Bulgaria to Cape Emine on the Black Sea...

 and struck deep into Bulgaria's north. The Bulgarians were completely surprised and the invaders seized Ovech, Shumen
Shumen
Shumen is the tenth-largest city in Bulgaria and capital of Shumen Province. In the period 1950–1965 it was called Kolarovgrad, after the name of the communist leader Vasil Kolarov...

, Madara
Madara (village)
Madara is a village in northeastern Bulgaria, part of Shumen municipality, Shumen Province. Madara lies east of the city of Shumen, at the western foot of the Madara plateau....

 and other towns. Due to the surprise campaign at first the towns and the castles were unable to organize proper defence but after the initial shock the Bulgarians took precautions. When the army of Ali Pasha besieged Varna
Varna
Varna is the largest city and seaside resort on the Bulgarian Black Sea Coast and third-largest in Bulgaria after Sofia and Plovdiv, with a population of 334,870 inhabitants according to Census 2011...

, the defenders stiffly resisted and the Turks were forced to abandon the siege and march northwards.

In Tutrakan
Tutrakan
Tutrakan is a town in northeastern Bulgaria, an administrative centre of the homonymous municipality, part of Silistra Province. It is situated on the right bank of the Danube opposite the Romanian town of Olteniţa , in the very west of Southern Dobruja, 58 km east of Rousse and 62 km...

 the citizens allowed the Turks to install a small garrison but then they killed the Turkish soldiers and prepared for siege. Ali Pasha immediately burned the surrounding fields and soon the starving town had to surrender. After this success they advanced to the west towards Nikopol
Nikopol, Bulgaria
Nikopol is a town in northern Bulgaria, the administrative center of Nikopol municipality, part of Pleven Province, on the right bank of the Danube river, 4 km downstream from the mouth of the Osam river. It spreads at the foot of steep chalk cliffs along the Danube and up a narrow valley...

, one of the strongest Bulgarian fortresses along the Danube
Danube
The Danube is a river in the Central Europe and the Europe's second longest river after the Volga. It is classified as an international waterway....

. The defence was organized by Ivan Shishman who was currently in the town. Although the Ottomans had nearly 30,000 men they could not take it and Ali Pasha had to seek reinforcements from Murad himself. According to Seadeddin the Sultan marched to Nikopol with an enormous army firmly decided to seize the town at all costs. When Ivan Shishman faced the new enemy he sought a truce. Murad agreed and the Bulgarians saved Nikopol but were forced to cede another key Danubian fortress, Silistra
Silistra
Silistra is a port city of northeastern Bulgaria, lying on the southern bank of the lower Danube at the country's border with Romania. Silistra is the administrative centre of Silistra Province and one of the important cities of the historical region of Southern Dobrudzha...

. However, when Ali Pasha reached Silistra, the Bulgarians refused to surrender the town. Murad besieged Nikopol for a second time and this time Ivan Shishman agreed to the Ottoman conditions and a Turkish garrison was installed in Silistra.

As a result of the campaign the Turks took most of eastern Bulgaria including several key towns. Now the authority of Ivan Shishman reduced to the lands to the west of the capital Tarnovo and several castles along the Danube. To the east the Bulgarians kept Varna and the capital of the Principality of Karvuna
Principality of Karvuna
The Principality of Karvuna or Despotate of Dobruja was a 14th-century quasi-independent state in the region of modern Dobruja. It emerged as a polity under the influence of the Byzantine Empire, and probably had a population composed of Bulgarians, Gagauz, Greeks, Tatars, and Vlachs.The...

, Kaliakra
Kaliakra
Kaliakra is a long and narrow headland in the Southern Dobruja region of the northern Bulgarian Black Sea Coast, located 12 km east of Kavarna and 60 km northeast of Varna. The coast is steep with vertical cliffs reaching 70 m down to the sea....

. Probably at that time Ivan Sratsimir
Ivan Sratsimir of Bulgaria
Ivan Sratsimir or Ivan Stratsimir was emperor of Bulgaria in Vidin from 1356 to 1396. He was born in 1324 or 1325, and he died in or after 1397. Despite being the eldest surviving son of Ivan Alexander, Ivan Sratsimir was disinherited in favour of his half-brother Ivan Shishman and proclaimed...

became an Ottoman vassal.
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