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| 1928 |
| | | Caribbean-born author Jean Rhys publishes her first novel, Postures, based on her affair with the writer Ford Madox Ford | |
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| 1930 |
| | | Rafael Trujillo establishes a dictatorship in the Dominican Republic that will last for 30 years | |
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| c. 1930 |
| | | The steel-band tradition begins to develop in Trinidad, with adapted metal objects taking the place of traditional skin drums | |
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| c. 1930 |
| | | The Rastafarian cult evolves in Jamaica, viewing Ras Tafari, the emperor of Ethiopia, as the black Messiah | |
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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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| 1934 |
| | | The US military government is finally withdrawn from Haiti after nineteen years | |
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| 1948 |
| | | The British government advertises in Jamaica for people to come and work in Britain | |
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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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