Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  13-06-1999 Trinidad en Tobago vs Cuba | 2 n.s.d. - 1 | Caribbean Cup, Finale Caribbean Cup | 1999 |
Troostfinale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
  13-06-1999 Jamaica vs Haïti | NIET GESPEELD | Caribbean Cup, Troostfinale Caribbean Cup | 1999 |
Halve Finale
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
| 11-06-1999 Trinidad en Tobago vs Haïti | 6 - 1 | Caribbean Cup, Halve Finale Caribbean Cup | 1999 | ||
| 10-06-1999 Cuba vs Jamaica | 2 - 0 | Caribbean Cup, Halve Finale Caribbean Cup | 1999 |
Groep A
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 07-06-1999 Jamaica vs Grenada | 2 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1999 | 3 | ||
 07-06-1999 Trinidad en Tobago vs Guadeloupe | 3 - 2 | Caribbean Cup, Caribbean Cup, Groep A | 1999 | 3 | ||
| 05-06-1999 Jamaica vs Guadeloupe | 5 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1999 | 2 | ||
| 05-06-1999 Trinidad en Tobago vs Grenada | 7 - 0 | Caribbean Cup, Caribbean Cup, Groep A | 1999 | 2 | ||
| 03-06-1999 Trinidad en Tobago vs Jamaica | 1 - 0 | Caribbean Cup, Caribbean Cup, Groep A | 1999 | 1 | ||
| 03-06-1999 Grenada vs Guadeloupe | 2 - 1 | Caribbean Cup, Caribbean Cup, Groep A | 1999 | 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 | 11 | 2 | 9 | 9 |
| 2 |  Jamaica | Halve Finale | #4eee37 | 3 | 2 | 0 | 1 | 7 | 3 | 4 | 6 |
| 3 |  Grenada | - | - | 3 | 1 | 0 | 2 | 3 | 10 | -7 | 3 |
| 4 |  Guadeloupe | - | - | 3 | 0 | 0 | 3 | 4 | 10 | -6 | 0 |
Groep B
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
 08-06-1999 Haïti vs Brazilië U20 | 4 - 3 | Caribbean Cup, Caribbean Cup, Groep B | 1999 | 3 | ||
 08-06-1999 Cuba vs Saint Kitts en Nevis | 2 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1999 | 3 | ||
| 06-06-1999 Cuba vs Brazilië U20 | 1 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1999 | 2 | ||
| 06-06-1999 Haïti vs Saint Kitts en Nevis | 2 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1999 | 2 | ||
| 04-06-1999 Brazilië U20 vs Saint Kitts en Nevis | 5 - 0 | Caribbean Cup, Caribbean Cup, Groep B | 1999 | 1 | ||
| 04-06-1999 Cuba vs Haïti | 3 - 1 | Caribbean Cup, Caribbean Cup, Groep B | 1999 | 1 |
STand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  Cuba | Halve Finale | #4eee37 | 3 | 2 | 1 | 0 | 6 | 1 | 5 | 7 |
| 2 |  Haïti | Halve Finale | #4eee37 | 3 | 2 | 0 | 1 | 7 | 6 | 1 | 6 |
| 3 |  Brazilië U20 | - | - | 3 | 1 | 0 | 2 | 8 | 5 | 3 | 3 |
| 4 |  Saint Kitts en Nevis | - | - | 3 | 0 | 0 | 3 | 0 | 9 | -9 | 0 |
Kwalificatie Ronde
Groep 1
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
  09-05-1999 Kaaimaneilanden vs Bahama’s | 4 - 1 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep F | 1999 | 3 | ||
 09-05-1999 Bermuda vs Cuba | 1 - 2 | Kwalificatie Gold Cup, Kwalificatie Gold Cup Caribische Groep F | 1999 | 3 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Cuba | Caribbean Cup 1999 | #4eee37 | 3 | 3 | 0 | 0 | 13 | 2 | 11 | 9 |
| 2 |  Bermuda | - | - | 3 | 2 | 0 | 1 | 11 | 3 | 8 | 6 |
| 3 |  Kaaimaneilanden | - | - | 3 | 1 | 0 | 2 | 6 | 9 | -3 | 3 |
| 4 |  Bahama’s | - | - | 3 | 0 | 0 | 3 | 1 | 17 | -16 | 0 |
Groep 2
| Date | Match | Time/Results | League | Season | Ground | Match Day |
|---|---|---|---|---|---|---|
  14-03-1999 Antigua en Barbuda vs Dominica | 1 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 1999 | 3 | ||
 14-03-1999 Guadeloupe vs Barbados | 1 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 1999 | 3 | ||
| 12-03-1999 Barbados vs Dominica | 3 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 1999 | 2 | ||
| 12-03-1999 Guadeloupe vs Antigua en Barbuda | 2 - 1 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 1999 | 2 | ||
| 10-03-1999 Barbados vs Antigua en Barbuda | 2 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 1999 | 1 | ||
| 10-03-1999 Guadeloupe vs Dominica | 1 - 0 | Kwalificatie Caribbean Cup, Kwalificatie Caribbean Cup: Groep 7 | 1999 | 1 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Guadeloupe | Caribbean Cup 1999 | #4eee37 | 3 | 3 | 0 | 0 | 4 | 1 | 3 | 9 |
| 2 |  Barbados | - | - | 3 | 2 | 0 | 1 | 5 | 2 | 3 | 6 |
| 3 |  Antigua en Barbuda | - | - | 3 | 0 | 1 | 2 | 2 | 5 | -3 | 1 |
| 3 |  Dominica | - | - | 3 | 0 | 1 | 2 | 2 | 5 | -3 | 1 |
Voorronde
Groep A
| Date | Match | Time/Results | League | Season | Ground |
|---|---|---|---|---|---|
 28-02-1999 Bahama’s vs Amerikaanse Maagdeneilanden | 0 - 0 | Kwalificatie Gold Cup, Voorronde Kwalificatie Gold Cup, Groep 1 | 1999 | ||
 26-02-1999 Turks- en Caicoseilanden vs Amerikaanse Maagdeneilanden | 2 - 2 | Kwalificatie Gold Cup, Voorronde Kwalificatie Gold Cup, Groep 1 | 1999 | ||
| 24-02-1999 Bahama’s vs Turks- en Caicoseilanden | 3 - 0 | Kwalificatie Gold Cup, Voorronde Kwalificatie Gold Cup, Groep 1 | 1999 |
Stand
| Pos | Club | Opmerking | Kleur | P | W | D | L | F | A | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Bahama’s | Volgende Ronde | #4eee37 | 2 | 1 | 1 | 0 | 3 | 0 | 3 | 4 |
| 2 |  Amerikaanse Maagdeneilanden | - | - | 2 | 0 | 2 | 0 | 2 | 2 | 0 | 2 |
| 3 |  Turks- en Caicoseilanden | - | - | 2 | 0 | 1 | 1 | 2 | 5 | -3 | 1 |