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| Date | Match | Score |
|---|---|---|
| 05.01.2026 | Tivoli Gardens - Portmore United | 2 : 2 |
| 31.08.2025 | Portmore United - Tivoli Gardens | 0 : 0 |
| 09.03.2025 | Portmore United - Tivoli Gardens | 1 : 1 |
| 06.01.2025 | Tivoli Gardens - Portmore United | 1 : 1 |
| 01.10.2024 | Portmore United - Tivoli Gardens | 2 : 1 |
| 25.02.2024 | Tivoli Gardens - Portmore United | 0 : 0 |
| 28.11.2023 | Portmore United - Tivoli Gardens | 0 : 0 |
| 09.04.2023 | Portmore United - Tivoli Gardens | 2 : 1 |
| 08.01.2023 | Tivoli Gardens - Portmore United | 0 : 0 |
| 04.04.2022 | Portmore United - Tivoli Gardens | 1 : 1 |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.09.2026 | Portmore United - Mount Pleasant Academy | 0 - 1 | L |
| 04.09.2026 | Cavalier - Portmore United | 0 - 2 | W |
| 04.08.2026 | Portmore United - Salcedo | 1 - 2 | L |
| 25.05.2026 | Portmore United - Cavalier | 2 - 2 | D |
| 20.05.2026 | Mount Pleasant Academy - Portmore United | 2 - 4 | 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 |