Head-to-head
Aggregate
Played10
Draws330.0%
Goals Bermuda20
Goals Cayman Islands8
Bermuda winsdrawsCayman Islands wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 04 Jun 2025 | Bermuda | 5–0 | Cayman Islands | H |
|
| 08 Jun 2021 | Bermuda | 1–1 | Cayman Islands | D |
|
| 31 Aug 2008 | Cayman Islands | 0–0 | Bermuda | D | ITL · CFU Caribbean Cup qualification |
| 30 Mar 2008 | Cayman Islands | 1–3 | Bermuda | A |
|
| 03 Feb 2008 | Bermuda | 1–1 | Cayman Islands | D |
|
| 24 Nov 2004 | Cayman Islands | 1–2 | Bermuda | A | ITL · CFU Caribbean Cup qualification |
| 11 Sep 1999 | Bermuda | 1–0 | Cayman Islands | H | ITL · Friendly |
| 09 Sep 1999 | Bermuda | 3–1 | Cayman Islands | H | ITL · Friendly |
| 07 May 1999 | Bermuda | 4–1 | Cayman Islands | H | ITL · CFU Caribbean Cup qualification |
| 10 May 1998 | Cayman Islands | 2–0 | Bermuda | H | ITL · CFU Caribbean Cup qualification |