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| 1492 |
| | | Columbus and his fellow explorers make landfall on the largest of the Caribbean islands, Cuba | |
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| 1493 |
| | | Columbus returns to Spain, landing at Palos with news of his great discoveries | |
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| 1493 |
| | | Pope Alexander VI draws a line through the Atlantic, dividing new discoveries between Spain (west) and Portugal (east) | |
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| 1494 |
| | | In negotiations about the New World at Tordesillas, the king of Portugal insists on a new demarcation line which later brings him Brazil | |
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| 1496 |
| | | Diego Columbus, brother of the explorer, establishes the first secure Spanish colony at Santo Domingo | |
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| 1497 |
| | | Henry VII commissions the Italian navigator John Cabot to cross the Atlantic in search of new territories for England | |
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| 1497 |
| | | John Cabot, searching for a trade route to China, probably reaches Newfoundland | |
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| c. 1500 |
| | | The Portuguese establish trading posts in east Africa, on the coast of Mozambique | |
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| c. 1500 |
| | | European diseases bring death on a massive scale to an American population that has no immunity | |
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| 1502 |
| | | Vasco da Gama wins a trading treaty for Portuguese merchants after bombarding the Indian port of Calicut into submission | |
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