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| Date | Match | Score |
|---|---|---|
| 24.04.2026 | Mount Pleasant Academy - Chapelton | 5 : 2 |
| 01.02.2026 | Chapelton - Mount Pleasant Academy | 0 : 2 |
| 12.10.2025 | Mount Pleasant Academy - Chapelton | 3 : 1 |
| 14.04.2025 | Chapelton - Mount Pleasant Academy | 0 : 2 |
| 20.02.2025 | Mount Pleasant Academy - Chapelton | 1 : 0 |
| 19.11.2024 | Chapelton - Mount Pleasant Academy | 1 : 1 |
| 25.04.2023 | Mount Pleasant Academy - Chapelton | 7 : 0 |
| 22.01.2023 | Chapelton - Mount Pleasant Academy | 0 : 3 |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.09.2026 | Portmore United - Mount Pleasant Academy | 0 - 1 | W |
| 03.09.2026 | Salcedo - Mount Pleasant Academy | 1 - 1 | D |
| 18.08.2026 | Mount Pleasant Academy - Cibao | 1 - 2 | L |
| 02.08.2026 | Mount Pleasant Academy - Delfines Del Este | 1 - 0 | W |
| 31.07.2026 | Mount Pleasant Academy - Robin Hood | 3 - 1 | W |
| 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 |