Head-to-head
Aggregate
Played4
Draws125.0%
Goals Anguilla7
Goals Montserrat6
Anguilla winsdrawsMontserrat wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 08 Feb 2001 | Anguilla | 4–1 | Montserrat | H | ITL · CFU Caribbean Cup qualification |
| 02 Apr 1995 | Anguilla | 0–1 | Montserrat | A | ITL · CFU Caribbean Cup qualification |
| 26 Mar 1995 | Montserrat | 3–2 | Anguilla | H | ITL · CFU Caribbean Cup qualification |
| 14 May 1991 | Anguilla | 1–1 | Montserrat | D | ITL · CFU Caribbean Cup qualification |