Jan. 1, 1959 - Dictator Fulgencio Batista flees Cuba and Fidel Castro's rebels take power.
February 1960 - Soviet Deputy Prime Minister Anastas Mikoyan visits Cuba, signs sugar and oil deals, first of many pacts over next 30 years.
June 1960 - Cuba nationalizes US-owned oil refineries after they refuse to process Soviet oil. Nearly all other US businesses expropriated by October.
October 1960 - Washington bans exports to Cuba, other than food and medicine.
April 16, 1961 - Castro declares Cuba socialist state.
April 17, 1961 - 1,297 Cuban exiles supported by CIA invade at Bay of Pigs; attack collapses two days later.
Jan. 22, 1962 - Cuba suspended from Organization of American States; Cuba responds with call for armed revolt across Latin America.
Feb, 7, 1962 - Washington bans all Cuban imports.
October 1962 - President Kennedy orders blockade of Cuba to force removal of Soviet nuclear-armed missiles; Soviets agree within days and Kennedy agrees privately not to invade Cuba.
March 1968 - Castro's government takes over almost all private businesses other than small farms.
July 1972 - Cuba joins Comecon, Soviet-led economic bloc.
April 1980 - Refugee crisis starts at Mariel port as Cuba says anyone can leave; some 125,000 Cubans flee by end of September.
December 1991 - Collapse of Soviet Union ends extensive aid and trade for Cuba; economic output plunges 35 percent by 1994.
August 1994 - Castro declares he will not stop Cubans trying to leave; some 40,000 take to sea heading for United States. Expanded US-Cuba migration agreement signed in September.
October 1997 - Castro reaffirms younger brother, Raul Castro, as successor.
Jan. 21-25, 1998 - Pope John Paul II visits Cuba.
June 23, 2001 - Castro faints briefly giving speech in searing sun, stunning Cubans and forcing many for first time to accept his eventual mortality.
Dec. 16, 2001 - Shipments of corn and chicken arrive in Havana harbor, the first direct US food sales to Cuba in nearly 40 years.
March 6, 2003 - Parliament elects Castro to sixth 5-year term as president of Council of State, Cuba's supreme governing body.
March 18, 2003 - Cuba cracks down on dissidents it alleges work with US; 75 sentenced to prison terms ranging from six to 28 years.
Oct. 20, 2004 - Castro trips and falls after speech, shattering left kneecap and breaking right arm, underscoring advancing age.
November 2004 - Cuba releases half-dozen political prisoners, including dissident writer Raul Rivero, in move widely seen as intended to court favor with European Union.
Feb. 2, 2005 - Castro calls President Bush "deranged" for referring to Cuba as outpost of tyranny.
July 27, 2006 - Castro's final personal appearance as president: A four-hour Revolution Day speech urging Cubans to have patience that electrical problems will be solved.
July 31, 2006 - Castro temporarily cedes power to brother to recover from operation for gastrointestinal bleeding.
Aug. 13, 2006 - Castro turns 80. Birthday celebrations postponed to December to give him more recovery time.
Dec. 2, 2006 - Castro fails to appear at military parade marking the 50th anniversary of Cuba's Revolutionary Armed Forces, does not attend any of his birthday celebrations.
March 28, 2007 - Castro writes the first dozens of essays called "Reflections of the Commander in Chief" that give him a voice on international affairs while he remains off the public stage.
June 18, 2007 - Castro's sister-in-law Vilma Espin, Raul's longtime wife and a former fellow rebel fighter, dies at age 77.
Aug. 13, 2007 - Castro turns 81, again failing to appear in public.
Oct. 14, 2007 - Castro makes live broadcast telephone call to ally Hugo Chavez, who tells him, "You will never die."
Dec. 18, 2007 - Castro publishes essay saying he doesn't intend to cling to power forever, will not "obstruct the path of younger people." Repeats the theme 10 days later in letter to parliament.
Jan. 20, 2008 - Castro re-elected to parliament, leaving open possibility could remain as president.
Feb. 19, 2008 - Castro resigns as president, apparently will remain in parliament.