Who would win if they met today?
Match averages
Biggest wins
All meetings (2)
| Date | Home | Score | Away | Result | Competition |
|---|---|---|---|---|---|
| 16 Nov 2025 | Cayman Islands | 4 - 0 | Anguilla | W | International Friendly |
| 04 Oct 2010 | Cayman Islands | 4 - 1 | Anguilla | W | UNCAF Concacaf Gold Cup C… |
By venue
Competitions faced in
International Friendly
UNCAF Concacaf Gold Cup Caribbean Zone
Year-by-year
| Year | Cayman … | D | Anguilla |
|---|---|---|---|
| 2025 | 1 | 0 | 0 |
| 2010 | 1 | 0 | 0 |
About this head-to-head
Cayman Islands and Anguilla have met 2 times on record. Cayman Islands lead with 2 wins, Anguilla have won 0 times and the two clubs have drawn 0 matches between them. Their first recorded meeting was on 04 October 2010.
This page is the permanent head-to-head hub for Cayman Islands vs Anguilla. Every future meeting between these two clubs will be added to this page automatically, so bookmark it for the latest results, biggest wins, venue records and competition breakdown. Visit the team pages for full squads, standings and upcoming fixtures: Cayman Islands and Anguilla.
Across their recorded meetings, Cayman Islands have found the net 8 times against Anguilla, while Anguilla have scored 1 time in reply — a combined 9 goals shared between the two sides. Their most recent fixture was played on 16 November 2025, the latest chapter in a rivalry stretching back to 2010. Follow every upcoming Cayman Islands versus Anguilla clash on SportScore for live scores, starting lineups, minute-by-minute commentary and a head-to-head record that updates automatically once the full-time whistle blows.