Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  15-12-2008 Jamaica vs Grenada | 2 - 0 | Caribbean Cup, Finale Caribbean Cup | 2008 |
Troostfinale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  14-12-2008 Cuba vs Guadeloupe | 0 - 0 w.n.s. | Caribbean Cup, Troostfinale Caribbean Cup | 2008 |
Halve Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
| 12-12-2008 Jamaica vs Guadeloupe | 2 - 0 | Caribbean Cup, Halve Finale Caribbean Cup | 2008 | ||
| 12-12-2008 Cuba vs Grenada | 2 - 2 w.n.s. | Caribbean Cup, Halve Finale Caribbean Cup | 2008 |
Groep A
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 08-12-2008 Cuba vs Haïti | 0 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 2008 | 3 | ||
 08-12-2008 Antigua en Barbuda vs Guadeloupe | 2 - 2 | Caribbean Cup, Caribbean Cup, Groep A | 2008 | 3 | ||
| 06-12-2008 Haïti vs Guadeloupe | 2 - 3 | Caribbean Cup, Caribbean Cup, Groep A | 2008 | 2 | ||
| 06-12-2008 Cuba vs Antigua en Barbuda | 3 - 0 | Caribbean Cup, Caribbean Cup, Groep A | 2008 | 2 | ||
| 04-12-2008 Haïti vs Antigua en Barbuda | 1 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 2008 | 1 | ||
| 04-12-2008 Guadeloupe vs Cuba | 1 - 2 | Caribbean Cup, Caribbean Cup, Groep A | 2008 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Cuba | Halve Finale | #4eee37 | 3 | 2 | 0 | 1 | 5 | 2 | 3 | 6 |
| 2 |  Guadeloupe | Halve Finale | #4eee37 | 3 | 1 | 1 | 1 | 6 | 6 | 0 | 4 |
| 3 |  Haïti | - | - | 3 | 1 | 1 | 1 | 4 | 4 | 0 | 4 |
| 4 |  Antigua en Barbuda | - | - | 3 | 0 | 2 | 1 | 3 | 6 | -3 | 2 |
Groep B
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 07-12-2008 Jamaica vs Trinidad en Tobago | 1 - 1 | Caribbean Cup, Caribbean Cup, Groep B | 2008 | 3 | ||
 07-12-2008 Grenada vs Barbados | 4 - 2 | Caribbean Cup, Caribbean Cup, Groep B | 2008 | 3 | ||
| 05-12-2008 Barbados vs Trinidad en Tobago | 1 - 2 | Caribbean Cup, Caribbean Cup, Groep B | 2008 | 2 | ||
| 05-12-2008 Jamaica vs Grenada | 4 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 2008 | 2 | ||
| 03-12-2008 Trinidad en Tobago vs Grenada | 1 - 2 | Caribbean Cup, Caribbean Cup, Groep B | 2008 | 1 | ||
| 03-12-2008 Jamaica vs Barbados | 2 - 1 | Caribbean Cup, Caribbean Cup, Groep B | 2008 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Jamaica | Halve Finale | #4eee37 | 3 | 2 | 1 | 0 | 7 | 2 | 5 | 7 |
| 2 |  Grenada | Halve Finale | #4eee37 | 3 | 2 | 0 | 1 | 6 | 7 | -1 | 6 |
| 3 |  Trinidad en Tobago | - | - | 3 | 1 | 1 | 1 | 4 | 4 | 0 | 4 |
| 4 |  Barbados | - | - | 3 | 0 | 0 | 3 | 4 | 8 | -4 | 0 |
Kwalificatieronde
Groep F
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 15-10-2008 Guadeloupe vs Martinique | 3 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 6 | 2008 | 3 | ||
 15-10-2008 Grenada vs Kaaimaneilanden | 4 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 6 | 2008 | 3 | ||
| 13-10-2008 Kaaimaneilanden vs Martinique | 0 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 6 | 2008 | 2 | ||
| 13-10-2008 Guadeloupe vs Grenada | 2 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 6 | 2008 | 2 | ||
| 11-10-2008 Guadeloupe vs Kaaimaneilanden | 7 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 6 | 2008 | 1 | ||
| 11-10-2008 Martinique vs Grenada | 2 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 6 | 2008 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Guadeloupe | Caribbean Cup 2008 | #4eee37 | 3 | 3 | 0 | 0 | 12 | 3 | 9 | 9 |
| 2 | Grenada | Caribbean Cup 2008 | #4eee37 | 3 | 1 | 1 | 1 | 7 | 6 | 1 | 4 |
| 3 |  Martinique | - | - | 3 | 1 | 1 | 1 | 4 | 5 | -1 | 4 |
| 4 |  Kaaimaneilanden | - | - | 3 | 0 | 0 | 3 | 3 | 12 | -9 | 0 |
Groep G
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 27-08-2008 Cuba vs Suriname | 6 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 2008 | 3 | ||
 27-10-2008 Nederlandse Antillen vs Barbados | 1 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 2008 | 3 | ||
| 25-10-2008 Cuba vs Barbados | 1 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 2008 | 2 | ||
| 25-10-2008 Suriname vs Nederlandse Antillen | 2 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 2008 | 2 | ||
| 23-10-2008 Barbados vs Suriname | 3 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 2008 | 1 | ||
| 23-10-2008 Cuba vs Nederlandse Antillen | 7 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 2008 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Cuba | Caribbean Cup 2008 | #4eee37 | 3 | 2 | 1 | 0 | 14 | 2 | 12 | 7 |
| 2 | Barbados | Caribbean Cup 2008 | #4eee37 | 3 | 2 | 1 | 0 | 6 | 4 | 2 | 7 |
| 3 |  Suriname | - | - | 3 | 1 | 0 | 2 | 4 | 10 | -6 | 3 |
| 4 |  Nederlandse Antillen | - | - | 3 | 0 | 0 | 3 | 3 | 11 | -8 | 0 |
Groep H
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 09-11-2008 Trinidad en Tobago vs Guyana | 1 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep H | 2008 | 3 | ||
 09-11-2008 Saint Kitts en Nevis vs Antigua en Barbuda | 3 - 4 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep H | 2008 | 3 | ||
| 07-11-2008 Trinidad en Tobago vs Saint Kitts en Nevis | 3 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep H | 2008 | 2 | ||
| 07-11-2008 Antigua en Barbuda vs Guyana | 2 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep H | 2008 | 2 | ||
| 05-11-2008 Trinidad en Tobago vs Antigua en Barbuda | 3 - 2 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep H | 2008 | 1 | ||
| 05-11-2008 Guyana vs Saint Kitts en Nevis | 1 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep H | 2008 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Trinidad en Tobago | Caribbean Cup 2008 | #4eee37 | 3 | 2 | 1 | 0 | 7 | 4 | 3 | 7 |
| 2 | Antigua en Barbuda | Caribbean Cup 2008 | #4eee37 | 3 | 2 | 0 | 1 | 8 | 7 | 1 | 6 |
| 3 |  Guyana | - | - | 3 | 0 | 2 | 1 | 3 | 4 | -1 | 2 |
| 4 |  Saint Kitts en Nevis | - | - | 3 | 0 | 1 | 2 | 5 | 8 | -3 | 1 |
Voorronde
Groep A
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
| 31-07-2008 Nederlandse Antillen vs Grenada | 2 - 0 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep A | 2008 | 3 | ||
 29-07-2008 Grenada vs Aruba | 3 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep A | 2008 | 2 | ||
| 27-07-2008 Nederlandse Antillen vs Aruba | 0 - 0 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep A | 2008 | 1 |
STand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Nederlandse Antillen | Kwalificatieronde | #4eee37 | 2 | 1 | 1 | 0 | 2 | 0 | 2 | 4 |
| 2 | Grenada | Kwalificatieronde | #4eee37 | 2 | 1 | 0 | 1 | 3 | 3 | 0 | 3 |
| 3 |  Aruba | - | - | 2 | 0 | 1 | 1 | 1 | 3 | -2 | 1 |
Groep B
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
| 10-08-2008 Guyana vs Suriname | 1 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 2008 | 3 | ||
 09-08-2008 Dominica vs Suriname | 1 - 3 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 2008 | 2 | ||
| 08-08-2008 Guyana vs Dominica | 3 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 2008 | 1 |
Stand
Groep C
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 31-08-2008 Kaaimaneilanden vs Bermuda | 0 - 0 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep C | 2008 | 3 | ||
 31-08-2008 Antigua en Barbuda vs Saint-Martin | 3 - 2 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep C | 2008 | 3 | ||
| 30-08-2008 Kaaimaneilanden vs Antigua en Barbuda | 1 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep C | 2008 | 2 | ||
| 30-08-2008 Saint-Martin vs Bermuda | 0 - 7 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep C | 2008 | 2 | ||
| 27-08-2008 Bermuda vs Antigua en Barbuda | 0 - 4 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep C | 2008 | 1 | ||
| 27-08-2008 Kaaimaneilanden vs Saint-Martin | 3 - 0 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep C | 2008 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Antigua en Barbuda | Volgende Ronde | #4eee37 | 3 | 2 | 1 | 0 | 8 | 3 | 5 | 7 |
| 2 | Kaaimaneilanden | Volgende Ronde | #4eee37 | 3 | 1 | 2 | 0 | 4 | 1 | 3 | 5 |
| 3 |  Bermuda | - | - | 3 | 1 | 1 | 1 | 7 | 4 | 3 | 4 |
| 4 |  Saint-Martin | - | - | 3 | 0 | 0 | 3 | 2 | 13 | -11 | 0 |
Groep D
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
| 28-09-2008 Saint Kitts en Nevis vs Barbados | 1 - 3 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 2008 | 3 | ||
 26-09-2008 Britse Maagdeneilanden vs Barbados | 1 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 2008 | 2 | ||
| 24-09-2008 Saint Kitts en Nevis vs Britse Maagdeneilanden | 4 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 2008 | 1 |
STand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Barbados | Kwalificatieronde | #4eee37 | 2 | 2 | 0 | 0 | 5 | 2 | 3 | 6 |
| 2 | Saint Kitts en Nevis | Kwalificatieronde | #4eee37 | 2 | 1 | 0 | 1 | 5 | 3 | 2 | 3 |
| 3 |  Britse Maagdeneilanden | - | - | 2 | 0 | 0 | 2 | 1 | 6 | -5 | 0 |
Groep E
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 19-09-2008 Martinique vs Anguilla | 3 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep E | 2008 | 3 | ||
 17-09-2008 Saint Vincent en de Grenadines vs Anguilla | 3 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep E | 2008 | 2 | ||
| 15-09-2008 Martinique vs Saint Vincent en de Grenadines | 3 - 0 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep E | 2008 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Martinique | Volgende Ronde | #4eee37 | 2 | 2 | 0 | 0 | 6 | 1 | 5 | 6 |
| 2 |  Saint Vincent en de Grenadines | - | - | 2 | 1 | 0 | 1 | 3 | 4 | -1 | 3 |
| 3 |  Anguilla | - | - | 2 | 0 | 0 | 2 | 2 | 6 | -4 | 0 |