Head-to-head
Aggregate
Played5
Draws120.0%
Goals Sint Maarten11
Goals Anguilla1
Sint Maarten winsdrawsAnguilla wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 22 Aug 2018 | Sint Maarten | 1–1 | Anguilla | D | ITL · Friendly |
| 13 Mar 2016 | Sint Maarten | 2–0 | Anguilla | H | ITL · Friendly |
| 02 Apr 1997 | Sint Maarten | 3–0 | Anguilla | H | ITL · CFU Caribbean Cup qualification |
| 29 Mar 1996 | Sint Maarten | 4–0 | Anguilla | H | ITL · CFU Caribbean Cup qualification |
| 06 Apr 1993 | Anguilla | 0–1 | Sint Maarten | A | ITL · CFU Caribbean Cup qualification |