Head-to-head
Aggregate
Played2
Draws00.0%
Goals Cayman Islands8
Goals Anguilla1
Cayman Islands winsdrawsAnguilla wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 15 Nov 2025 | Cayman Islands | 4–0 | Anguilla | H | ITL · CONCACAF Series |
| 04 Oct 2010 | Cayman Islands | 4–1 | Anguilla | H | ITL · CFU Caribbean Cup qualification |