Head-to-head
Aggregate
Played13
Draws215.4%
Goals Cuba43
Goals Cayman Islands4
Cuba winsdrawsCayman Islands wins
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 11 Jun 2024 | Cuba | 3–0 | Cayman Islands | H |
|
| 06 Sep 2006 | Cuba | 7–0 | Cayman Islands | H | ITL · CFU Caribbean Cup qualification |
| 27 Mar 2004 | Cuba | 3–0 | Cayman Islands | H |
|
| 22 Feb 2004 | Cayman Islands | 1–2 | Cuba | A |
|
| 27 Nov 2002 | Cayman Islands | 0–5 | Cuba | A | ITL · Gold Cup qualification |
| 19 Mar 2000 | Cayman Islands | 0–0 | Cuba | D |
|
| 05 Mar 2000 | Cuba | 4–0 | Cayman Islands | H |
|
| 05 May 1999 | Cuba | 4–1 | Cayman Islands | H | ITL · CFU Caribbean Cup qualification |
| 06 May 1998 | Cayman Islands | 2–2 | Cuba | D | ITL · CFU Caribbean Cup qualification |
| 14 May 1996 | Cayman Islands | 0–5 | Cuba | A |
|
| 12 May 1996 | Cayman Islands | 0–1 | Cuba | A |
|
| 26 Apr 1996 | Cayman Islands | 0–4 | Cuba | A | ITL · CFU Caribbean Cup qualification |
| 30 Jul 1995 | Cayman Islands | 0–3 | Cuba | A | ITL · CFU Caribbean Cup |