- CFU Digicel Caribbean Championship Jamaica 2008 Qualifying
- CONCACAF Gold Cup United States 2009
CONCACAF Gold Cup United States 2009 Qualifying - Stage 1
- Stage 2
Stage 1
- Group A (Trinidad & Tobago, Jamaica, Barbados, Grenada)
- Group B (Haiti, Cuba, Antigua & Barbuda, Guadeloupe)
| Date | Venue | Team | Result | Team |
|---|---|---|---|---|
| (78) Trinidad & Tobago, (139) Grenada | ||||
| 3 December 2008 | Kingston (Jamaica) | Trinidad & Tobago | (0) 1-2 (1) | Grenada |
| (83) Jamaica, (100) Barbados | ||||
| 3 December 2008 | Kingston (Jamaica) | Jamaica | (0) 2-1 (1) | Barbados |
| (78) Trinidad & Tobago, (100) Barbados | ||||
| 5 December 2008 | Montego Bay (Jamaica) | Trinidad & Tobago | (1) 2-1 (1) | Barbados |
| (83) Jamaica, (139) Grenada | ||||
| 5 December 2008 | Montego Bay (Jamaica) | Jamaica | (2) 4-0 (0) | Grenada |
| (100) Barbados, (139) Grenada | ||||
| 7 December 2008 | Falmouth (Jamaica) | Barbados | (0) 2-4 (3) | Grenada |
| (78) Trinidad & Tobago, (83) Jamaica | ||||
| 7 December 2008 | Falmouth (Jamaica) | Jamaica | (0) 1-1 (0) | Trinidad & Tobago |
| Team | P | W | D | L | GF - GA | GD | Pts |
|---|---|---|---|---|---|---|---|
| Jamaica | 3 | 2 | 1 | 0 | 7-2 | (5) | 7 |
| Grenada | 3 | 2 | 0 | 1 | 6-7 | (-1) | 6 |
| Trinidad & Tobago | 3 | 1 | 1 | 1 | 4-4 | (0) | 4 |
| Barbados | 3 | 0 | 0 | 3 | 4-8 | (-4) | 0 |
| Date | Venue | Team | Result | Team |
|---|---|---|---|---|
| (105) Haiti, (133) Antigua & Barbuda | ||||
| 4 December 2008 | Montego Bay (Jamaica) | Haiti | (0) 1-1 (0) | Antigua & Barbuda |
| (73) Cuba, Guadeloupe | ||||
| 4 December 2008 | Montego Bay (Jamaica) | Cuba | (1) 2-1 (1) | Guadeloupe |
| (73) Cuba, (133) Antigua & Barbuda | ||||
| 6 December 2008 | Falmouth (Jamaica) | Cuba | (3) 3-0 (0) | Antigua & Barbuda |
| (105) Haiti, Guadeloupe | ||||
| 6 December 2008 | Falmouth (Jamaica) | Haiti | (1) 2-3 (2) | Guadeloupe |
| (73) Cuba, (105) Haiti | ||||
| 8 December 2008 | Montego Bay (Jamaica) | Cuba | (0) 0-1 (1) | Haiti |
| (133) Antigua & Barbuda, Guadeloupe | ||||
| 8 December 2008 | Montego Bay (Jamaica) | Antigua & Barbuda | (1) 2-2 (1) | Guadeloupe |
| Team | P | W | D | L | GF - GA | GD | Pts |
|---|---|---|---|---|---|---|---|
| Cuba | 3 | 2 | 0 | 1 | 5-2 | (3) | 6 |
| Guadeloupe | 3 | 1 | 1 | 1 | 6-6 | (0) | 4 |
| Haiti | 3 | 1 | 1 | 1 | 4-4 | (0) | 4 |
| Antigua & Barbuda | 3 | 0 | 2 | 1 | 3-6 | (-3) | 2 |
Stage 2
| Grenada (Final) Cuba (Place 3) |
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| Date | Venue | Team | Result | Team |
|---|---|---|---|---|
| (73) Cuba, (139) Grenada | ||||
| 11 December 2008 | Kingston (Jamaica) | Cuba | (2) (2) 2-2 (2) (1) 5-6 |
Grenada |
| Jamaica (Host) (Final) Guadeloupe (Place 3) |
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| Date | Venue | Team | Result | Team |
|---|---|---|---|---|
| (83) Jamaica, Guadeloupe | ||||
| 11 December 2008 | Kingston (Jamaica) | Jamaica | (1) 2-0 (0) | Guadeloupe |
| (3) Guadeloupe (4) Cuba |
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| Date | Venue | Team | Result | Team |
|---|---|---|---|---|
| (73) Cuba, Guadeloupe | ||||
| 14 December 2008 | Kingston (Jamaica) | Cuba | (0) (0) 0-0 (0) (0) 4-5 |
Guadeloupe |
| (1) Jamaica (Host) (CFU Caribbean Championship Jamaica 2008) (2) Grenada |
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| Date | Venue | Team | Result | Team |
|---|---|---|---|---|
| (83) Jamaica, (139) Grenada | ||||
| 14 December 2008 | Kingston (Jamaica) | Jamaica | (1) 2-0 (0) | Grenada |