Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  13-07-1997 Trinidad en Tobago vs Saint Kitts en Nevis | 4 - 0 | Caribbean Cup, Finale Caribbean Cup | 1997 |
Troostfinale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  13-07-1997 Jamaica vs Grenada | 4 - 1 | Caribbean Cup, Troostfinale Caribbean Cup | 1997 |
Halve Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
| 10-07-1997 Grenada vs Saint Kitts en Nevis | 1 - 2 n.v. | Caribbean Cup, Halve Finale Caribbean Cup | 1997 | ||
| 10-07-1997 Trinidad en Tobago vs Jamaica | 1 w.n.s. - 1 | Caribbean Cup, Halve Finale Caribbean Cup | 1997 |
Groep A
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 08-07-1997 Antigua en Barbuda vs Jamaica | 0 - 2 | Caribbean Cup, Caribbean Cup, Groep A | 1997 | 3 | ||
| 06-07-1997 Antigua en Barbuda vs Grenada | 1 - 3 | Caribbean Cup, Caribbean Cup, Groep A | 1997 | 2 | ||
| 04-07-1997 Grenada vs Jamaica | 1 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1997 | 1 |
STand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Grenada | Halve Finale | #4eee37 | 2 | 1 | 1 | 0 | 4 | 2 | 2 | 4 |
| 2 |  Jamaica | Halve Finale | #4eee37 | 2 | 1 | 1 | 0 | 3 | 1 | 2 | 4 |
| 3 |  Antigua en Barbuda | - | - | 2 | 0 | 0 | 2 | 1 | 5 | -4 | 0 |
Groep B
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
| 08-07-1997 Saint Kitts en Nevis vs Trinidad en Tobago | 0 - 3 | Caribbean Cup, Caribbean Cup, Groep B | 1997 | 3 | ||
 06-07-1997 Martinique vs Saint Kitts en Nevis | 0 - 2 | Caribbean Cup, Caribbean Cup, Groep B | 1997 | 2 | ||
| 04-07-1997 Martinique vs Trinidad en Tobago | 2 - 1 | Caribbean Cup, Caribbean Cup, Groep B | 1997 | 1 |
STand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Trinidad en Tobago | Halve Finale | #4eee37 | 2 | 1 | 0 | 1 | 4 | 2 | 2 | 3 |
| 2 |  Martinique | - | - | 2 | 1 | 0 | 1 | 2 | 3 | -1 | 3 |
| 3 |  Saint Kitts en Nevis | Halve Finale | #4eee37 | 2 | 1 | 0 | 1 | 2 | 3 | -1 | 3 |
Kwalificatie
Groep 2
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
 27-02-1997 Jamaica vs Bermuda | 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 1997 | ||
| 21-02-1997 Jamaica vs Bermuda | 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 2 | 1997 |
Kaaimaneilanden en Puerto Rico trokken zich terug.
Groep 4
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
  06-04-1997 Sint Maarten vs Britse Maagdeneilanden | 3 - 2 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1997 | 3 | ||
  06-04-1997 Dominica vs Anguilla | 5 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1997 | 3 | ||
| 04-04-1997 Britse Maagdeneilanden vs Anguilla | 4 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1997 | 2 | ||
| 04-04-1997 Dominica vs Sint Maarten | 1 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1997 | 2 | ||
| 02-04-1997 Dominica vs Britse Maagdeneilanden | 6 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1997 | 1 | ||
| 02-04-1997 Sint Maarten vs Anguilla | 3 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 4 | 1997 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Dominica | Play-Offs | #4eee37 | 3 | 3 | 0 | 0 | 12 | 1 | 11 | 9 |
| 2 |  Sint Maarten | - | - | 3 | 2 | 0 | 1 | 6 | 3 | 3 | 6 |
| 3 |  Britse Maagdeneilanden | - | - | 3 | 1 | 0 | 2 | 7 | 10 | -3 | 3 |
| 4 |  Anguilla | - | - | 3 | 0 | 0 | 3 | 1 | 12 | -11 | 0 |