Head-to-head
Aggregate
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 01 Jun 2025 | Grenada | 2–0 | Anguilla | H | ITL · Friendly |
| 15 Apr 1998 | Grenada | 14–1 | Anguilla | H | ITL · CFU Caribbean Cup qualification |