1209    Otto IV is crowned emperor of the Holy Roman Empire by Pope Innocent III.

1346    Charles IV of Luxembourg is elected emperor of the Holy Roman Empire.

1519    Charles V is elected Emperor of the Holy Roman Empire.

1555    After 18 months of siege, Siena surrenders to the Florentine-Imperial army. The Republic of Siena is incorporated into the Grand Duchy of Tuscany.

1619    Ferdinand II is elected emperor of the Holy Roman Empire.

1631    The city of Magdeburg in Germany is seized by forces of the Holy Roman Empire and most of its inhabitants massacred, in one of the bloodiest incidents of the Thirty Years' War.

1632    Battle of Rain; Swedes under Gustavus Adolphus defeat the Holy Roman Empire during the Thirty Years' War.

1636    The Swedish Army defeats the armies of Saxony and the Holy Roman Empire at the Battle of Wittstock.

1645    Thirty Years' War: the Second Battle of Nördlingen sees French forces defeating those of the Holy Roman Empire.

1697    The Treaty of Rijswijk is signed by France, England, Spain, the Holy Roman Empire and the Dutch Republic ending the Nine Years' War (1688–97).

1719    The Principality of Liechtenstein is created within the Holy Roman Empire.

1757    Seven Years' War: Frederick the Great defeats the allied armies of France and the Holy Roman Empire at the Battle of Rossbach.

1806    Sixteen German imperial states leave the Holy Roman Empire and form the Confederation of the Rhine.

1806    Francis II, the last Holy Roman Emperor, abdicates ending the Holy Roman Empire.