1964 Summer Olympics |
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| Two Person Heavyweight Dinghy, Open | Firebird II | 19 | |
| Rawle Barrow • Cordell Barrow | |||
1972 Summer Olympics |
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| Two Person Heavyweight Dinghy, Open | Trinidad and Tobago | 28 | |
| David Farfan • Richard Bennett | |||
1984 Summer Olympics |
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| One Person Dinghy, Open | Jean-Marc Holder | 20 | |
2012 Summer Olympics |
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| One Person Dinghy, Men | Andrew Lewis | 37 | |
2014 Summer Youth Olympics |
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| One Person Dinghy, Girls | Abigail Affoo | 28 | |
2016 Summer Olympics |
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| One Person Dinghy, Men | Andrew Lewis | 39 | |
2020 Summer Olympics |
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| One Person Dinghy, Men | Andrew Lewis | 29 | |