| Nov. 3, 2000 | CFU | 2000 | B | Paradise SC | 1 - 2 | Violette AC | Jamaica | 1 | |||
| Nov. 1, 2000 | CFU | 2000 | B | Harbour View | 1 - 0 | Paradise SC | Jamaica | 1 | |||
| Oct. 30, 2000 | CFU | 2000 | B | Paradise SC | 1 - 0 | Roots Alley Ballers | Jamaica | 1 | |||
| July 29, 1990 | CCL | 1990 | 2 | Caribbean | Paradise SC | np | SV Transvaal | Dover, Barbados | 1 | ||
| July 16, 1990 | CCL | 1990 | 2 | Caribbean | Paradise SC | 0 - 2 | SV Transvaal | Dover, Barbados | 1 | ||
| April 8, 1990 | CCL | 1990 | 1 | Caribbean | Paradise SC | 1 - 1 | Zenith (Guadeloupe) | Dover, Barbados | 1 | ||
| March 31, 1990 | CCL | 1990 | 1 | Caribbean | Paradise SC | 2 - 0 | Zenith (Guadeloupe) | Dover, Barbados | 1 |