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| Date | Match | Score |
|---|---|---|
| 08.03.2026 | Tivoli Gardens - Dunbeholden | 2 : 1 |
| 21.12.2025 | Dunbeholden - Tivoli Gardens | 1 : 0 |
| 19.03.2025 | Dunbeholden - Tivoli Gardens | 2 : 4 |
| 19.01.2025 | Tivoli Gardens - Dunbeholden | 2 : 0 |
| 21.11.2024 | Dunbeholden - Tivoli Gardens | 2 : 1 |
| 10.03.2024 | Tivoli Gardens - Dunbeholden | 1 : 1 |
| 10.12.2023 | Dunbeholden - Tivoli Gardens | 2 : 2 |
| 05.03.2023 | Dunbeholden - Tivoli Gardens | 4 : 1 |
| 03.12.2022 | Tivoli Gardens - Dunbeholden | 0 : 2 |
| 08.05.2022 | Dunbeholden - Tivoli Gardens | 1 : 1 |
| Date | Match | Score | Res |
|---|---|---|---|
| 06.05.2026 | Waterhouse - Dunbeholden | 4 - 0 | L |
| 03.05.2026 | Dunbeholden - Mount Pleasant Academy | 0 - 5 | L |
| 26.04.2026 | Treasure Beach - Dunbeholden | 1 - 0 | L |
| 23.04.2026 | Dunbeholden - Harbour View | 4 - 0 | W |
| 19.04.2026 | Dunbeholden - Tivoli Gardens | 2 - 0 | 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 |