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| Date | Match | Score |
|---|---|---|
| 07.12.2025 | Dunbeholden - Mount Pleasant Academy | 0 : 0 |
| 09.03.2025 | Dunbeholden - Mount Pleasant Academy | 0 : 3 |
| 05.01.2025 | Mount Pleasant Academy - Dunbeholden | 4 : 0 |
| 30.10.2024 | Dunbeholden - Mount Pleasant Academy | 3 : 2 |
| 28.01.2024 | Dunbeholden - Mount Pleasant Academy | 1 : 2 |
| 05.11.2023 | Mount Pleasant Academy - Dunbeholden | 3 : 0 |
| 23.05.2023 | Mount Pleasant Academy - Dunbeholden | 3 : 0 |
| 15.05.2023 | Dunbeholden - Mount Pleasant Academy | 1 : 1 |
| 07.05.2023 | Dunbeholden - Mount Pleasant Academy | 3 : 1 |
| 05.02.2023 | Mount Pleasant Academy - Dunbeholden | 1 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 06.05.2026 | Waterhouse - Dunbeholden | 4 - 0 | L |
| 03.05.2026 | Dunbeholden - Mount Pleasant Academy | 0 - 5 | L |
| 26.04.2026 | Treasure Beach - Dunbeholden | 1 - 0 | L |
| 23.04.2026 | Dunbeholden - Harbour View | 4 - 0 | W |
| 19.04.2026 | Dunbeholden - Tivoli Gardens | 2 - 0 | W |
| 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 |