Head-to-head
Aggregate
Played3
Draws133.3%
Goals Cayman Islands8
Goals Sint Maarten5
Cayman Islands winsdrawsSint Maarten wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 04 Mar 1994 | Cayman Islands | 5–0 | Sint Maarten | H | ITL · CFU Caribbean Cup qualification |
| 03 Apr 1992 | Sint Maarten | 4–2 | Cayman Islands | H | ITL · CFU Caribbean Cup qualification |
| 24 Mar 1990 | Sint Maarten | 1–1 | Cayman Islands | D | ITL · CFU Caribbean Cup qualification |