[3] Trinidad & Tobago 1-1 Jamaica [1] 2025-07-24 02:00
Stadium: Hasely Crawford Stadium Round: 5
Referee: Walter Lopez Castellanos Home Manager: Dwight Yorke Away Manager: Steve McClaren
Head to Head
| International Match | 2025/05/27 18:45 | Jamaica v Trinidad & Tobago | L | 3-2 |
| International Match | 2025/02/10 01:00 | Jamaica v Trinidad & Tobago | D | 1-1 |
| International Match | 2025/02/07 00:30 | Jamaica v Trinidad & Tobago | L | 1-0 |
| International Match | 2024/03/03 20:00 | Trinidad & Tobago v Jamaica | D | 0-0 |
| CONCACAF Gold Cup | 2023/06/28 23:30 | Jamaica v Trinidad & Tobago | L | 4-1 |
| International Match | 2023/03/15 00:00 | Jamaica v Trinidad & Tobago | D | 0-0 |
| International Match | 2023/03/11 23:00 | Jamaica v Trinidad & Tobago | W | 0-1 |
| International Match | 2017/08/25 00:00 | Trinidad & Tobago v Jamaica | L | 1-2 |
Home History
| CONCACAF Gold Cup | 2025/06/22 23:00 | Saudi Arabia v Trinidad & Tobago | D | 1-1 |
| CONCACAF Gold Cup | 2025/06/19 22:45 | Trinidad & Tobago v Haiti | D | 1-1 |
| CONCACAF Gold Cup | 2025/06/15 22:00 | USA v Trinidad & Tobago | L | 5-0 |
| North & Central America - World Cup Qualifying | 2025/06/11 01:00 | Costa Rica v Trinidad & Tobago | L | 2-1 |
| North & Central America - World Cup Qualifying | 2025/06/06 23:30 | Trinidad & Tobago v St. Kitts and Nevis | W | 6-2 |
| International Match | 2025/05/31 11:30 | Trinidad & Tobago v Ghana | L | 0-4 |
| International Match | 2025/05/27 18:45 | Jamaica v Trinidad & Tobago | L | 3-2 |
| CONCACAF Gold Cup Qualifying | 2025/03/25 23:00 | Trinidad & Tobago v Cuba | W | 4-0 |
Away History
| CONCACAF Gold Cup | 2025/06/24 23:00 | Panama v Jamaica | L | 4-1 |
| CONCACAF Gold Cup | 2025/06/20 23:45 | Jamaica v Guadeloupe | W | 2-1 |
| CONCACAF Gold Cup | 2025/06/17 02:00 | Jamaica v Guatemala | L | 0-1 |
| North & Central America - World Cup Qualifying | 2025/06/10 23:00 | Jamaica v Guatemala | W | 3-0 |
| North & Central America - World Cup Qualifying | 2025/06/07 19:00 | British Virgin Islands v Jamaica | W | 0-1 |
| International Match | 2025/05/31 16:00 | Jamaica v Nigeria | D | 2-2 |
| International Match | 2025/05/27 18:45 | Jamaica v Trinidad & Tobago | W | 3-2 |
| CONCACAF Gold Cup Qualifying | 2025/03/26 00:00 | Jamaica v St. Vincent/Grenadines | W | 3-0 |