Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  30-07-1995 Trinidad en Tobago vs Saint Vincent en de Grenadines | 5 - 0 | Caribbean Cup, Finale Caribbean Cup | 1995 |
Troostfinale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  30-07-1995 Kaaimaneilanden vs Cuba | 0 - 3 | Caribbean Cup, Troostfinale Caribbean Cup | 1995 |
Halve Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
| 28-07-1995 Kaaimaneilanden vs Trinidad en Tobago | 2 - 9 | Caribbean Cup, Halve Finale Caribbean Cup | 1995 | ||
| 27-07-1995 Saint Vincent en de Grenadines vs Cuba | 3 - 2 | Caribbean Cup, Halve Finale Caribbean Cup | 1995 |
Groep A
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
  25-07-1995 Antigua en Barbuda vs Frans-Guyana | 2 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1995 | 3 | ||
| 25-07-1995 Kaaimaneilanden vs Saint Vincent en de Grenadines | 2 - 2 | Caribbean Cup, Caribbean Cup, Groep A | 1995 | 3 | ||
| 23-07-1995 Kaaimaneilanden vs Frans-Guyana | 1 - 0 | Caribbean Cup, Caribbean Cup, Groep A | 1995 | 2 | ||
| 23-07-1995 Antigua en Barbuda vs Saint Vincent en de Grenadines | 1 - 5 | Caribbean Cup, Caribbean Cup, Groep A | 1995 | 2 | ||
| 21-07-1995 Frans-Guyana vs Saint Vincent en de Grenadines | 1 - 3 | Caribbean Cup, Caribbean Cup, Groep A | 1995 | 1 | ||
| 21-07-1995 Kaaimaneilanden vs Antigua en Barbuda | 2 - 0 | Caribbean Cup, Caribbean Cup, Groep A | 1995 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Saint Vincent en de Grenadines | Halve Finale | #4eee37 | 3 | 2 | 1 | 0 | 10 | 4 | 6 | 7 |
| 2 |  Kaaimaneilanden | Halve Finale | #4eee37 | 3 | 2 | 1 | 0 | 5 | 2 | 3 | 7 |
| 3 |  Antigua en Barbuda | - | - | 3 | 1 | 0 | 2 | 3 | 8 | -5 | 3 |
| 4 |  Frans-Guyana | - | - | 3 | 0 | 0 | 3 | 2 | 6 | -4 | 0 |
Groep B
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 23-07-1995 Jamaica vs Trinidad en Tobago | 1 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1995 | 3 | ||
 23-07-1995 Cuba vs Saint Lucia | 2 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1995 | 3 | ||
| 21-07-1995 Saint Lucia vs Trinidad en Tobago | 0 - 5 | Caribbean Cup, Caribbean Cup, Groep B | 1995 | 2 | ||
| 21-07-1995 Jamaica vs Cuba | 1 - 2 | Caribbean Cup, Caribbean Cup, Groep B | 1995 | 2 | ||
| 19-07-1995 Jamaica vs Saint Lucia | 2 - 1 | Caribbean Cup, Caribbean Cup, Groep B | 1995 | 1 | ||
| 19-07-1995 Cuba vs Trinidad en Tobago | 0 - 2 | Caribbean Cup, Caribbean Cup, Groep B | 1995 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Trinidad en Tobago | Halve Finale | #4eee37 | 3 | 2 | 0 | 1 | 7 | 1 | 6 | 6 |
| 2 |  Cuba | Halve Finale | #4eee37 | 3 | 2 | 0 | 1 | 4 | 3 | 1 | 6 |
| 3 |  Jamaica | - | - | 3 | 2 | 0 | 1 | 4 | 3 | 1 | 6 |
| 4 |  Saint Lucia | - | - | 3 | 0 | 0 | 3 | 1 | 9 | -8 | 0 |
Kwalificatie
Groep 4
Tweede Ronde
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
 07-05-1995 Montserrat vs Saint Vincent en de Grenadines | 0 - 11 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1995 | ||
| 01-05-1995 Saint Vincent en de Grenadines vs Montserrat | 9 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1995 |
Eerste Ronde
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
 26-03-1995 Montserrat vs Anguilla | 3 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1995 | ||
 26-03-1995 Dominica vs Saint Vincent en de Grenadines | 0 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1995 | ||
| 02-04-1995 Saint Vincent en de Grenadines vs Dominica | 0 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1995 | ||
| 02-04-1995 Anguilla vs Montserrat | 0 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1995 |
Groep 5
Tweede Ronde
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
 21-05-1995 Antigua en Barbuda vs Saint Kitts en Nevis | 2 w.n.s. - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 5 | 1995 | ||
| 30-04-1995 Saint Kitts en Nevis vs Antigua en Barbuda | 1 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 5 | 1995 |
Eerste Ronde
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
 19-03-1995 Sint Maarten vs Saint Kitts en Nevis | 0 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 5 | 1995 | ||
| 26-03-1995 Saint Kitts en Nevis vs Sint Maarten | 0 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 5 | 1995 | ||
 26-03-1995 Antigua en Barbuda vs Britse Maagdeneilanden | NIET GESPEELD | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 5 | 1995 |