Head-to-head
Aggregate
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 14 Oct 2025 | Jamaica | 4–0 | Bermuda | H |
|
| 05 Sep 2025 | Bermuda | 0–4 | Jamaica | A |
|
| 23 Feb 1997 | Jamaica | 3–2 | Bermuda | H | ITL · CFU Caribbean Cup qualification |
| 21 Feb 1997 | Jamaica | 1–0 | Bermuda | H | ITL · CFU Caribbean Cup qualification |
| 08 Nov 1992 | Jamaica | 3–2 | Bermuda | H |
|
| 25 Oct 1992 | Bermuda | 1–1 | Jamaica | D |
|
| 12 Apr 1992 | Jamaica | 0–0 | Bermuda | D | ITL · Friendly |
| 12 Sep 1991 | Bermuda | 1–1 | Jamaica | D | ITL · Friendly |
| 27 Dec 1972 | Bermuda | 0–3 | Jamaica | A | ITL · Friendly |
| 24 Dec 1972 | Bermuda | 0–0 | Jamaica | D | ITL · Friendly |
| 28 Dec 1965 | Bermuda | 0–3 | Jamaica | A | ITL · Friendly |