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| 1898 |
| | | Theodore Roosevelt fights against the Spanish in Cuba with a volunteer regiment of cavalry, the Rough Riders | |
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| 1898 |
| | | In the Treaty of Paris, ending the Spanish-American War, Spain cedes Puerto Rico and Cuba to the USA | |
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| 1902 |
| | | Cuba becomes independent after three years of US military rule, with certain restrictions imposed by the Platt Amendment of 1901 | |
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| 1903 |
| | | Cuba is forced to accept a permanent US military presence in Guantanamo Bay | |
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| 1912 |
| | | President Taft sends US marines to Cuba because of political unrest in the island | |
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| 1933 |
| | | Fulgencio Batista, as army chief of staff, begins a long career running the affairs of Cuba | |
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| 1956 |
| | | Communist activist Fidel Castro returns from Mexico to Cuba to organize guerrilla warfare against the Batista regime | |
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| 1958 |
| | | Dictator Fulgencio Batista flees from Cuba, leaving Havana open to Fidel Castro and his victorious guerrillas | |
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| 1959 |
| | | Fidel Castro begins more than four decades of authoritarian rule in Cuba | |
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| 1961 |
| | | An invasion force of about 1500 Cuban exiles comes ashore in Cuba's Bay of Pigs in an attempt to topple the Castro regime | |
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