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| Date | Match | Score |
|---|---|---|
| 29.12.2025 | Tivoli Gardens - Chapelton | 2 : 0 |
| 24.08.2025 | Chapelton - Tivoli Gardens | 2 : 1 |
| 27.04.2025 | Chapelton - Tivoli Gardens | 2 : 2 |
| 12.02.2025 | Tivoli Gardens - Chapelton | 1 : 1 |
| 01.12.2024 | Chapelton - Tivoli Gardens | 2 : 3 |
| 20.02.2023 | Chapelton - Tivoli Gardens | 2 : 0 |
| 29.10.2022 | Tivoli Gardens - Chapelton | 3 : 0 |
| 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 |
| 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 |