| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 9/10/25 | Jamaica vs Trinidad and Tobago | World Cup - Qualification - Third Stage | 2:0 | No | No |
| 5/27/25 | Jamaica vs Trinidad and Tobago | Friendly International | 3:2 | Yes | Yes |
| 2/10/25 | Jamaica vs Trinidad and Tobago | Friendly International | 1:1 | No | Yes |
| 2/7/25 | Jamaica vs Trinidad and Tobago | Friendly International | 1:0 | No | No |
| 3/3/24 | Trinidad and Tobago vs Jamaica | Friendly International | 0:0 | No | No |
| 3/1/24 | Trinidad and Tobago vs Jamaica | Friendly International | 0:1 | No | No |
| 6/29/23 | Jamaica vs Trinidad and Tobago | Gold Cup | 4:1 | Yes | Yes |
| 3/15/23 | Jamaica vs Trinidad and Tobago | Friendly International | 0:0 | No | No |
| 3/12/23 | Jamaica vs Trinidad and Tobago | Friendly International | 0:1 | No | No |
| 3/12/23 | Trinidad and Tobago vs Jamaica | Friendly International | 1:0 | No | No |
| 8/25/17 | Trinidad and Tobago vs Jamaica | Friendly International | 1:2 | Yes | Yes |
| 11/19/14 | Jamaica vs Trinidad and Tobago | Caribbean Cup | 0:0 | No | No |
| 11/20/13 | Trinidad and Tobago vs Jamaica | Friendly International | 2:0 | No | No |
| 11/16/13 | Jamaica vs Trinidad and Tobago | Friendly International | 0:1 | No | No |
| 10/11/10 | Jamaica vs Trinidad and Tobago | Friendly International | 1:0 | No | No |
| 8/12/10 | Trinidad and Tobago vs Jamaica | Friendly International | 1:3 | Yes | Yes |
| 6/7/08 | Trinidad and Tobago vs Jamaica | Friendly International | 1:1 | No | Yes |
| 3/27/08 | Jamaica vs Trinidad and Tobago | Friendly International | 2:2 | Yes | Yes |
| 6/30/01 | Trinidad and Tobago vs Jamaica | World Cup - Qualification - Third Stage | 1:2 | Yes | Yes |
| 2/28/01 | Jamaica vs Trinidad and Tobago | World Cup - Qualification - Third Stage | 1:0 | No | No |
| 8/16/92 | Jamaica vs Trinidad and Tobago | World Cup - Qualification - Third Stage | 1:1 | No | Yes |
| 7/5/92 | Trinidad and Tobago vs Jamaica | World Cup - Qualification - Third Stage | 1:2 | Yes | Yes |