| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 8/26/25 | Dunbeholden vs Portmore United | Premier League | 0:2 | No | No |
| 4/27/25 | Dunbeholden vs Portmore United | Premier League | 1:0 | No | No |
| 2/12/25 | Portmore United vs Dunbeholden | Premier League | 0:0 | No | No |
| 12/1/24 | Dunbeholden vs Portmore United | Premier League | 3:3 | Yes | Yes |
| 2/4/24 | Portmore United vs Dunbeholden | Premier League | 1:1 | No | Yes |
| 11/12/23 | Dunbeholden vs Portmore United | Premier League | 0:2 | No | No |
| 3/20/23 | Dunbeholden vs Portmore United | Premier League | 1:3 | Yes | Yes |
| 12/21/22 | Portmore United vs Dunbeholden | Premier League | 0:0 | No | No |
| 5/29/22 | Dunbeholden vs Portmore United | Premier League | 1:0 | No | No |
| 3/15/22 | Portmore United vs Dunbeholden | Premier League | 2:3 | Yes | Yes |
| 6/27/21 | Portmore United vs Dunbeholden | Premier League | 2:0 | No | No |
| 1/30/20 | Dunbeholden vs Portmore United | Premier League | 1:4 | Yes | Yes |
| 12/1/19 | Portmore United vs Dunbeholden | Premier League | 1:2 | Yes | Yes |
| 9/15/19 | Portmore United vs Dunbeholden | Premier League | 0:1 | No | No |
| 3/20/19 | Portmore United vs Dunbeholden | Premier League | 2:0 | No | No |
| 12/2/18 | Dunbeholden vs Portmore United | Premier League | 0:1 | No | No |
| 11/18/18 | Dunbeholden vs Portmore United | Premier League | 2:3 | Yes | Yes |