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| | | | The Caribbean (West Indies) |
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| 1882 |
| | | Ulises Heureaux becomes dictator of the Dominican Republic and retains power until assassinated in 1899 | |
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| 1897 |
| | | The Spanish governor in Cuba is recalled to Spain, for pioneering the concept of the concentration camp | |
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| 1898 |
| | | The US battleship Maine is blown up in Havana harbour, sparking off the Spanish-American War | |
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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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| 1900 |
| | | Puerto Ricans are granted limited democracy in a bill of rigfhts introduced after two years of US military occupation | |
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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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| 1915 |
| | | Woodrow Wilson sends US marines to take control in Haiti after a spate of political assassinations | |
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