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| Date | Match | Score |
|---|---|---|
| 07.09.2025 | Chapelton - Portmore United | 3 : 2 |
| 23.03.2025 | Portmore United - Chapelton | 0 : 1 |
| 22.01.2025 | Chapelton - Portmore United | 0 : 3 |
| 20.10.2024 | Portmore United - Chapelton | 2 : 0 |
| 06.03.2023 | Portmore United - Chapelton | 0 : 0 |
| 04.12.2022 | Chapelton - Portmore United | 0 : 1 |
| Date | Match | Score | Res |
|---|---|---|---|
| 06.05.2026 | Chapelton - Arnett Gardens | 2 - 7 | L |
| 03.05.2026 | Waterhouse - Chapelton | 3 - 0 | L |
| 26.04.2026 | Chapelton - Spanish Town Police | 6 - 2 | W |
| 24.04.2026 | Mount Pleasant Academy - Chapelton | 5 - 2 | L |
| 19.04.2026 | Chapelton - Portmore United | 0 - 2 | L |
| 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 |