Head-to-head
Aggregate
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 30 Mar 2021 | Barbados | 1–0 | Anguilla | H |
|
| 24 Sep 2006 | Barbados | 7–1 | Anguilla | H | ITL · CFU Caribbean Cup qualification |