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| Date | Match | Score |
|---|---|---|
| 06.05.2026 | Mount Pleasant Academy - Montego Bay United | 2 : 1 |
| 28.12.2025 | Montego Bay United - Mount Pleasant Academy | 0 : 1 |
| 24.08.2025 | Mount Pleasant Academy - Montego Bay United | 2 : 2 |
| 18.05.2025 | Mount Pleasant Academy - Montego Bay United | 1 : 1 |
| 16.05.2025 | Montego Bay United - Mount Pleasant Academy | 0 : 1 |
| 20.04.2025 | Mount Pleasant Academy - Montego Bay United | 2 : 0 |
| 25.02.2025 | Montego Bay United - Mount Pleasant Academy | 1 : 1 |
| 24.11.2024 | Mount Pleasant Academy - Montego Bay United | 3 : 0 |
| 25.02.2024 | Mount Pleasant Academy - Montego Bay United | 1 : 1 |
| 27.11.2023 | Montego Bay United - Mount Pleasant Academy | 1 : 2 |
| 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 |
|---|---|---|---|
| 24.05.2026 | Mount Pleasant Academy - Montego Bay United | 2 - 3 | W |
| 21.05.2026 | Montego Bay United - Cavalier | 0 - 2 | L |
| 17.05.2026 | Cavalier - Montego Bay United | 0 - 1 | W |
| 06.05.2026 | Mount Pleasant Academy - Montego Bay United | 2 - 1 | L |
| 03.05.2026 | Montego Bay United - Treasure Beach | 0 - 2 | L |