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| Date | Match | Score |
|---|---|---|
| 04.03.2026 | Tivoli Gardens - Mount Pleasant Academy | 1 : 1 |
| 11.12.2025 | Mount Pleasant Academy - Tivoli Gardens | 5 : 0 |
| 30.03.2025 | Mount Pleasant Academy - Tivoli Gardens | 0 : 0 |
| 26.01.2025 | Tivoli Gardens - Mount Pleasant Academy | 0 : 1 |
| 27.10.2024 | Mount Pleasant Academy - Tivoli Gardens | 1 : 0 |
| 18.02.2024 | Mount Pleasant Academy - Tivoli Gardens | 1 : 0 |
| 23.11.2023 | Tivoli Gardens - Mount Pleasant Academy | 0 : 1 |
| 26.02.2023 | Tivoli Gardens - Mount Pleasant Academy | 0 : 2 |
| 30.11.2022 | Mount Pleasant Academy - Tivoli Gardens | 3 : 1 |
| 22.05.2022 | Mount Pleasant Academy - Tivoli Gardens | 4 : 1 |
| 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 | Portmore United - Tivoli Gardens | 3 - 0 | L |
| 03.05.2026 | Tivoli Gardens - Cavalier | 0 - 2 | L |
| 30.04.2026 | Treasure Beach - Tivoli Gardens | 4 - 2 | L |
| 27.04.2026 | Molynes United - Tivoli Gardens | 2 - 0 | L |
| 22.04.2026 | Montego Bay United - Tivoli Gardens | 5 - 1 | L |