1539    Spain annexes Cuba.

1715    A Spanish treasure fleet of 10 ships under Admiral Ubilla leaves Havana, Cuba for Spain. Seven days later, 9 of them sink in a storm off the coast of Florida. A few centuries later, treasure is salvaged from these wrecks.

1829    {{HMS|Pickle}} captures the armed slave ship ''Voladora'' off the coast of Cuba.

1839    Twenty miles off the coast of Cuba, 53 rebelling African slaves led by Joseph Cinqué take over the slave ship ''Amistad''.

1868    Carlos Céspedes issues the Grito de Yara from his plantation, La Demajagua, proclaiming Cuba's independence

1869    José Martí founds the Cuban Revolutionary Party.

1875    Notorious New York City politician Boss Tweed escapes from prison and flees to Cuba, then Spain.

1898    Spanish-American War: The {{USS|Maine|ACR-1|6}} explodes and sinks in Havana harbor in Cuba, killing more than 260. This event leads the United States to declare war on Spain.

1898    Spanish-American War: The United States Navy begins a blockade of Cuban ports and the {{USS|Nashville|PG-7|6}} captures a Spanish merchant ship.

1898    Spanish-American War: U.S. Marines land on the island of Cuba.

1898    Spanish-American War: U.S. war ships set sail for Cuba.

1898    Spanish-American War: United States Marines land in Cuba.

1898    Spanish-American War: The Spanish fleet, led by Pascual Cervera y Topete, is destroyed by the U.S. Navy in Santiago, Cuba.

1899    Spanish rule ends in Cuba.

1901    The U.S. Congress passes the Platt amendment, limiting the autonomy of Cuba as a condition for the withdrawal of American troops.

1902    Cuba gains independence from the United States. Tomás Estrada Palma becomes the country's first President.

1903    Cuba leases Guantánamo Bay to the United States "in perpetuity".

1909    United States troops leave Cuba with the exception of Guantanamo Bay Naval Base after being there since the Spanish-American War.

1911    The destroyer {{USS|Terry|DD-25}} makes the first airplane rescue at sea saving the life of James McCurdy 10 miles from Havana, Cuba.

1939    Holocaust: The {{MS|St. Louis}}, a ship carrying 963 Jewish refugees, is denied permission to land in Florida, United States, after already being turned away from Cuba. Forced to return to Europe, more than 200 of its passengers later die in Nazi concentration camps.

1941    World War II: The Republic of China, Cuba, Guatemala, the Provisional Government of the Republic of Korea, and the Philippine Commonwealth, declare war on Germany and Japan.

1949    Cuba recognizes Israel.

1952    Fulgencio Batista leads a successful coup in Cuba and appoints himself as the "provisional president".

1956    The ''Granma'' yacht reaches the shores of Cuba's Oriente province and Fidel Castro, Che Guevara and 80 other members of the 26th of July Movement disembark to initiate the Cuban Revolution.

1957    Cuban student revolutionaries storm the presidential palace in Havana in a failed attempt on the life of President Fulgencio Batista.

1957    Cuba: Fulgencio Batista bombs the revolt in Cienfuegos.

1959    Fulgencio Batista, president of Cuba, is overthrown by Fidel Castro's forces during the Cuban Revolution.

1959    The United States recognizes the new Cuban government of Fidel Castro.

1959    Fidel Castro becomes Premier of Cuba after dictator Fulgencio Batista was overthrown on January 1.

1959    A group of Dominican exiles with leftist tendencies that departed from Cuba land in the Dominican Republic with the intent of deposing Rafael Leónidas Trujillo Molina. Save for four of them, all are killed and/or executed by Trujillo's army.

1960    French freighter 'La Coubre' explodes in Havana, Cuba killing 100.

1960    U.S. President Dwight D. Eisenhower signs the National Security Council directive on the anti-Cuban covert action program that will ultimately lead to the Bay of Pigs Invasion.

1960    Cuban Revolution: in response to a United States embargo, Cuba nationalizes American and foreign-owned property in the nation.

1960    Fidel Castro arrives in New York City as the head of the Cuban delegation to the United Nations.

1961    The United States severs diplomatic relations with Cuba.

1961    Bay of Pigs Invasion: A group of CIA financed and trained Cuban refugees lands at the Bay of Pigs in Cuba with the aim of ousting Fidel Castro.

1961    The Bay of Pigs invasion of Cuba ends in success for the defenders.

1961    Failure of the Bay of Pigs Invasion of US-backed troops against Cuba.

1961    The Prime Minister of Cuba, Fidel Castro, proclaims Cuba a socialist nation and abolishes elections.

1961    In a nationally broadcast speech, Cuban leader Fidel Castro declares that he is a Marxist-Leninist and that Cuba is going to adopt Communism.

1962    The Organization of American States suspends Cuba's membership.

1962    The United States bans all Cuban imports and exports.

1962    The Soviet ship ''Poltava'' heads toward Cuba, one of the events that sets into motion the Cuban Missile Crisis.

1962    The Cuban Missile Crisis begins: A U.S. Air Force U-2 reconnaissance plane and its pilot fly over the island of Cuba and take photographs of Soviet missiles capable of carrying nuclear warheads being installed and erected in Cuba.

1962    Cuban Missile Crisis between the United States and Cuba begins.

1962    Cuban Missile Crisis: US President John F. Kennedy, after internal counsel from Dwight D. Eisenhower, announces that American reconnaissance planes have discovered Soviet nuclear weapons in Cuba, and that he has ordered a naval "quarantine" of the Communist nation.

1962    Cuban missile crisis: Adlai Stevenson shows photos at the UN proving Soviet missiles are installed in Cuba.

1962    Major Rudolf Anderson of the United States Air Force becomes the only direct human casualty of the Cuban Missile Crisis when his U-2 reconnaissance airplane is shot down in Cuba by a Soviet-supplied SA-2 Guideline surface-to-air missile.

1962    Cuban Missile Crisis: Soviet Union leader Nikita Khrushchev announces that he had ordered the removal of Soviet missile bases in Cuba.

1962    Cuban Missile Crisis ends: In response to the Soviet Union agreeing to remove its missiles from Cuba, U.S. President John F. Kennedy ends the quarantine of the Caribbean nation.

1963    Travel, financial and commercial transactions by United States citizens to Cuba are made illegal by the John F. Kennedy administration.

1965    Cuba and the United States formally agree to begin an airlift for Cubans who want to go to the United States. By 1971, 250,000 Cubans made use of this program.

1966    The Cuban Adjustment Act enters force, allowing 123,000 Cubans the opportunity to apply for permanent residence in the United States.

1970    October Crisis: In Montreal, Quebec, kidnapped British Trade Commissioner James Cross is released by the Front de libération du Québec terrorist group after being held hostage for 60 days. Police negotiate his release and in return the Canadian government grants five terrorists from the FLQ's Chenier Cell their request for safe passage to Cuba.

1972    Southern Airways Flight 49 from Birmingham, Alabama is hijacked and, at one point, is threatened with crashing into the nuclear installation at the Oak Ridge National Laboratory. After two days, the plane lands in Havana, Cuba, where the hijackers are jailed by Fidel Castro.

1976    Cuba: national Constitution is proclaimed.

1985    Radio Martí, part of the Voice of America service, begins broadcasting to Cuba.

1989    Soviet leader Mikhail Gorbachev arrives in Havana, Cuba to meet with Fidel Castro in an attempt to mend strained relations.

1990    The United States begins broadcasting TV Martí to Cuba in an effort to bridge the information blackout imposed by the Castro regime.

1995    A Cubana de Aviación Antonov An-24 crashes into the Caribbean off southeast Cuba killing 44 people.

2002    Former US President Jimmy Carter arrives in Cuba for a five-day visit with Fidel Castro becoming the first President of the United States, in or out of office, to visit the island since Castro's 1959 revolution.

2002    The Caribbean Community Heads of Government meet with the Government of Cuba and declare the date to be "CARICOM-Cuba Day"—to celebrate diplomatic ties between the Caribbean Community (CARICOM) and Cuba.

2004    Fidel Castro, Cuba's President, announces that transactions using the American Dollar will be banned by November 8.

2004    Cuba and Venezuela found the Bolivarian Alliance for the Americas.