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| Date | Match | Score |
|---|---|---|
| 22.03.2026 | Chapelton - Montego Bay United | 3 : 1 |
| 25.01.2026 | Montego Bay United - Chapelton | 2 : 0 |
| 05.10.2025 | Chapelton - Montego Bay United | 1 : 2 |
| 10.03.2025 | Chapelton - Montego Bay United | 0 : 1 |
| 05.01.2025 | Montego Bay United - Chapelton | 2 : 1 |
| 30.09.2024 | Chapelton - Montego Bay United | 0 : 1 |
| 26.03.2023 | Chapelton - Montego Bay United | 0 : 0 |
| 28.12.2022 | Montego Bay United - Chapelton | 1 : 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 |
|---|---|---|---|
| 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 |