Thursday 10 Jun 1999 · Port of Spain, Trinidad and Tobago (neutral)
No scorers on record for this match.
World Football Elo before kick-off, and what the result did to it.
Expected score for Cuba: 40.3% (a draw counts half). An upset — the lower-rated side won.
Meeting 19 of 31, 1930–2024.
Before
After
Before
After
From Cuba's side.
| 6 Sep 2024 | Jamaica | 0–0 | Away | CONCACAF Nations League 2024 | — |
| 30 Mar 2015 | Jamaica | 0–3 | Away | Friendly | — |
| 12 Dec 2012 | Jamaica | 1–0 | Neutral | CFU Caribbean Cup 2012 | — |
| 24 Feb 2012 | Jamaica | 0–3 | Away | Friendly | — |
| 22 Feb 2012 | Jamaica | 0–1 | Away | Friendly | — |
| 24 Feb 2005 | Jamaica | 0–1 | Neutral | CFU Caribbean Cup 2005 | — |
| 6 Jul 2003 | Jamaica | 2–1 | Away | Friendly | — |
| 13 Mar 2003 | Jamaica | 1–0 | Home | Friendly | — |
| 11 Mar 2003 | Jamaica | 0–0 | Home | Friendly | — |
| 20 Jul 2001 | Jamaica | 0–0 | Home | Friendly | — |
| 10 Jun 2001 | Jamaica | 1–4 | Away | Friendly | — |
| 2 Jul 2000 | Jamaica | 1–1 | Away | Friendly | — |
| 10 Jun 1999 | Jamaica | 2–0 | Neutral | CFU Caribbean Cup 1999 | — |
| 29 Jun 1997 | Jamaica | 0–3 | Away | Friendly | — |
| 14 Jan 1996 | Jamaica | 1–1 | Away | Friendly | — |
| 21 Jul 1995 | Jamaica | 2–1 | Away | CFU Caribbean Cup 1995 | — |
| 12 Mar 1995 | Jamaica | 0–0 | Away | Friendly | — |
| 22 Jun 1992 | Jamaica | 0–0 | Neutral | CFU Caribbean Cup 1992 | — |
| 29 Apr 1987 | Jamaica | 0–2 | Away | Friendly | — |
| 29 Aug 1976 | Jamaica | 2–0 | Home | CONCACAF Championship qualification 1976 | — |
Score: openfootball · Scorers: none · Line-ups: none · Cards: none