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| Date | Match | Score |
|---|---|---|
| 16.02.2026 | Waterhouse - Tivoli Gardens | 1 : 1 |
| 09.12.2025 | Tivoli Gardens - Waterhouse | 2 : 1 |
| 16.03.2025 | Tivoli Gardens - Waterhouse | 3 : 2 |
| 12.01.2025 | Waterhouse - Tivoli Gardens | 0 : 1 |
| 06.10.2024 | Tivoli Gardens - Waterhouse | 0 : 1 |
| 30.04.2024 | Tivoli Gardens - Waterhouse | 0 : 2 |
| 22.04.2024 | Waterhouse - Tivoli Gardens | 1 : 1 |
| 17.01.2024 | Waterhouse - Tivoli Gardens | 0 : 1 |
| 22.10.2023 | Tivoli Gardens - Waterhouse | 3 : 0 |
| 18.04.2023 | Tivoli Gardens - Waterhouse | 0 : 1 |
| Date | Match | Score | Res |
|---|---|---|---|
| 13.05.2026 | Waterhouse - Cavalier | 0 - 2 | L |
| 11.05.2026 | Cavalier - Waterhouse | 2 - 2 | D |
| 06.05.2026 | Waterhouse - Dunbeholden | 4 - 0 | W |
| 03.05.2026 | Waterhouse - Chapelton | 3 - 0 | W |
| 28.04.2026 | Mount Pleasant Academy - Waterhouse | 2 - 1 | L |
| 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 |