Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  07-06-1996 Trinidad en Tobago vs Cuba | 2 - 0 | Caribbean Cup, Finale Caribbean Cup | 1996 |
Troostfinale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  05-06-1996 Martinique vs Suriname | 1 w.n.s. - 1 | Caribbean Cup, Troostfinale Caribbean Cup | 1996 |
Halve Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
| 03-06-1996 Cuba vs Suriname | 4 - 0 | Caribbean Cup, Halve Finale Caribbean Cup | 1996 | ||
| 02-06-1996 Trinidad en Tobago vs Martinique | 2 n.v. - 1 | Caribbean Cup, Halve Finale Caribbean Cup | 1996 |
Groep A
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 30-05-1996 Suriname vs Saint Kitts en Nevis | 1 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1996 | 1 | ||
| 28-05-1996 Trinidad en Tobago vs Saint Kitts en Nevis | 5 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1996 | 3 | ||
 28-05-1996 Suriname vs Jamaica | 3 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1996 | 3 | ||
| 26-05-1996 Trinidad en Tobago vs Suriname | 3 - 0 | Caribbean Cup, Caribbean Cup, Groep A | 1996 | 2 | ||
| 26-05-1996 Jamaica vs Saint Kitts en Nevis | 4 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1996 | 2 | ||
| 24-05-1996 Trinidad en Tobago vs Jamaica | 1 - 0 | Caribbean Cup, Caribbean Cup, Groep A | 1996 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Trinidad en Tobago | Halve Finale | #4eee37 | 3 | 3 | 0 | 0 | 9 | 1 | 8 | 9 |
| 2 |  Suriname | Halve Finale | #4eee37 | 3 | 1 | 1 | 1 | 4 | 5 | -1 | 4 |
| 3 |  Jamaica | - | - | 3 | 1 | 0 | 2 | 5 | 5 | 0 | 3 |
| 4 |  Saint Kitts en Nevis | - | - | 3 | 0 | 1 | 2 | 3 | 10 | -7 | 1 |
Groep B
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 29-05-1996 Martinique vs Saint Vincent en de Grenadines | 3 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1996 | 3 | ||
 29-05-1996 Cuba vs Haïti | 0 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1996 | 3 | ||
| 27-05-1996 Haïti vs Saint Vincent en de Grenadines | 2 - 2 | Caribbean Cup, Caribbean Cup, Groep B | 1996 | 2 | ||
| 27-05-1996 Cuba vs Martinique | 1 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1996 | 2 | ||
| 25-05-1996 Martinique vs Haïti | 1 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1996 | 1 | ||
| 25-05-1996 Cuba vs Saint Vincent en de Grenadines | 2 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1996 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Cuba | Halve Finale | #4eee37 | 3 | 2 | 1 | 0 | 3 | 0 | 3 | 7 |
| 2 |  Martinique | Halve Finale | #4eee37 | 3 | 2 | 0 | 1 | 4 | 1 | 3 | 6 |
| 3 |  Haïti | - | - | 3 | 0 | 2 | 1 | 2 | 3 | -1 | 2 |
| 4 |  Saint Vincent en de Grenadines | - | - | 3 | 0 | 1 | 2 | 2 | 7 | -5 | 1 |
Kwalificatie
Groep 2
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 31-03-1996 Saint Kitts en Nevis vs Sint Maarten | 3 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 1996 | 3 | ||
 29-03-1996 Sint Maarten vs Anguilla | 4 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 1996 | 2 | ||
| 27-03-1996 Saint Kitts en Nevis vs Anguilla | 8 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 1996 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Saint Kitts en Nevis | Caribbean Cup 1996 | #4eee37 | 2 | 2 | 0 | 0 | 11 | 0 | 11 | 6 |
| 2 |  Sint Maarten | - | - | 2 | 1 | 0 | 1 | 4 | 3 | 1 | 3 |
| 3 |  Anguilla | - | - | 2 | 0 | 0 | 2 | 0 | 12 | -12 | 0 |