Head-to-head
Aggregate
Played3
Draws00.0%
Goals Anguilla3
Goals Saint Kitts and Nevis18
Anguilla winsdrawsSaint Kitts and Nevis wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 25 May 2025 | Anguilla | 2–4 | Saint Kitts and Nevis | A | ITL · Friendly |
| 22 Sep 2006 | Anguilla | 1–6 | Saint Kitts and Nevis | A | ITL · CFU Caribbean Cup qualification |
| 27 Mar 1996 | Saint Kitts and Nevis | 8–0 | Anguilla | H | ITL · CFU Caribbean Cup qualification |