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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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| 1957 |
| | | Barbadian cricketer Gary Sobers, playing in Kingston, Jamaica, against Pakistan, makes a record Test score of 365 not out | |
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| 1957 |
| | | A country doctor, François Duvalier, is elected president of Haiti on a massive popular vote | |
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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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| 1959 |
| | | West Indian poet and playwright Derek Walcott founds the Trinidad Theatre Workshop | |
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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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| 1961 |
| | | Two days after landing in the Bay of Pigs, 114 Cuban exiles are dead and about 1300 have been captured | |
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| 1961 |
| | | Caribbean novelist V.S. Naipaul features his Trinidad family in A House for Mr Biswas | |
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| 1961 |
| | | Rafael Trujillo, dictator of the Dominican Republic for the past 30 years, is killed by a machine-gun attack on his car | |
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