| COPA DEL CARIBE | ||||
| TRINIDAD Y TOBAGO 1999 | ||||
| Grupo A | Trinidad y Tobago | |||
| Grenada | ||||
| Guadalupe | ||||
| Jamaica | ||||
| 3-jun-1999 | Puerto España | Grenada | 2 | Roberts |
| Guadalupe | 1 | |||
| 3-jun-1999 | Puerto España | Trinidad y Tobago | 1 | John |
| Jamaica | 0 | |||
| 5-jun-1999 | Puerto España | Jamaica | 5 | Davis, Griffiths, Graham (3) |
| Guadalupe | 1 | Didier | ||
| 5-jun-1999 | Puerto España | Trinidad y Tobago | 7 | Prosper (3), Eve, Dwarika, Trotman (2) |
| Grenada | 0 | |||
| 7-jun-1999 | Puerto España | Jamaica | 2 | Graham, Fuller |
| Grenada | 1 | Roberts | ||
| 7-jun-1999 | Puerto España | Trinidad y Tobago | 3 | Prosper, Mason (2) |
| Guadalupe | 2 | Damas-Agis (2) | ||
| Grupo B | Brasil | |||
| Cuba | ||||
| Haiti | ||||
| Saint Kitts and Nevis | ||||
| 4-jun-1999 | Puerto España | Cuba | 3 | Marten (2), Alvarez |
| Haiti | 1 | Tardieu | ||
| 4-jun-1999 | Puerto España | Brasil | 5 | |
| Saint Kitts and Nevis | 0 | |||
| 6-jun-1999 | Puerto España | Haiti | 2 | Vorbe, Chevallier |
| Saint Kitts and Nevis | 0 | |||
| 6-jun-1999 | Puerto España | Brasil | 0 | |
| Cuba | 1 | Alvarez | ||
| 8-jun-1999 | Puerto España | Brasil | 3 | |
| Haiti | 4 | Tardieu | ||
| 8-jun-1999 | Puerto España | Cuba | 2 | Alvarez (2) |
| Saint Kitts and Nevis | 0 | |||
| Semifinales | ||||
| 10-jun-1999 | Puerto España | Cuba | 2 | Gandara (P), Alvarez |
| Jamaica | 0 | |||
| 11-jun-1999 | Puerto España | Trinidad y Tobago | 6 | Dwarila, Eve, Andrews, Trotman, Mason, John |
| Haiti | 1 | Chevalier | ||
| 3er Lugar | ||||
| 13-jun-1999 | Puerto España | Jamaica | ||
| Haiti | ||||
| (*) Partido cancelado por mala condicion del campo de juego, ambos comparten el tercer lugar. | ||||
| FINAL | ||||
| 13-sep-1999 | Puerto España | Trinidad y Tobago | 2 | Rougier, John |
| Cuba | 1 | Prado | ||
| Campeón: TRINIDAD Y TOBAGO | ||||