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| Date | Match | Score |
|---|---|---|
| 05.03.2026 | Portmore United - Waterhouse | 0 : 1 |
| 12.12.2025 | Waterhouse - Portmore United | 1 : 2 |
| 20.04.2025 | Portmore United - Waterhouse | 0 : 2 |
| 23.02.2025 | Waterhouse - Portmore United | 1 : 0 |
| 24.11.2024 | Portmore United - Waterhouse | 0 : 0 |
| 10.03.2024 | Portmore United - Waterhouse | 0 : 0 |
| 10.12.2023 | Waterhouse - Portmore United | 1 : 1 |
| 30.04.2023 | Portmore United - Waterhouse | 1 : 1 |
| 29.01.2023 | Waterhouse - Portmore United | 1 : 1 |
| 26.04.2022 | Waterhouse - Portmore United | 3 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.09.2026 | Portmore United - Mount Pleasant Academy | 0 - 1 | L |
| 04.09.2026 | Cavalier - Portmore United | 0 - 2 | W |
| 04.08.2026 | Portmore United - Salcedo | 1 - 2 | L |
| 25.05.2026 | Portmore United - Cavalier | 2 - 2 | D |
| 20.05.2026 | Mount Pleasant Academy - Portmore United | 2 - 4 | W |
| Date | Match | Score | Res |
|---|---|---|---|
| 13.05.2026 | Waterhouse - Cavalier | 0 - 2 | L |
| 11.05.2026 | Cavalier - Waterhouse | 2 - 2 | D |
| 06.05.2026 | Waterhouse - Dunbeholden | 4 - 0 | W |
| 03.05.2026 | Waterhouse - Chapelton | 3 - 0 | W |
| 28.04.2026 | Mount Pleasant Academy - Waterhouse | 2 - 1 | L |