Head-to-head
Aggregate
Played13
Draws17.7%
Goals Jamaica40
Goals Cayman Islands10
Jamaica winsdrawsCayman Islands wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 09 Sep 2018 | Jamaica | 4–0 | Cayman Islands | H | ITL · CONCACAF Nations League qualification |
| 28 Jun 2009 | Cayman Islands | 1–4 | Jamaica | A | ITL · Friendly |
| 09 Nov 2008 | Cayman Islands | 0–2 | Jamaica | A | ITL · Friendly |
| 27 Aug 2000 | Cayman Islands | 0–6 | Jamaica | A | ITL · Friendly |
| 09 Feb 2000 | Cayman Islands | 0–1 | Jamaica | A | ITL · Friendly |
| 06 Feb 2000 | Cayman Islands | 0–0 | Jamaica | D | ITL · Friendly |
| 24 Oct 1999 | Cayman Islands | 1–4 | Jamaica | A | ITL · Friendly |
| 22 Jul 1998 | Jamaica | 4–0 | Cayman Islands | H | ITL · CFU Caribbean Cup |
| 22 Oct 1995 | Cayman Islands | 1–5 | Jamaica | A | ITL · Friendly |
| 06 Mar 1994 | Cayman Islands | 3–2 | Jamaica | H | ITL · CFU Caribbean Cup qualification |
| 26 May 1991 | Jamaica | 3–2 | Cayman Islands | H | ITL · CFU Caribbean Cup |
| 06 May 1990 | Cayman Islands | 1–2 | Jamaica | A | ITL · Friendly |
| 07 Feb 1987 | Cayman Islands | 1–3 | Jamaica | A | ITL · Friendly |