| :: H2H ( Chapelton Chapelton - Portmore United Portmore United ) :: |
| 23.01.2025 | | Chapelton Chapelton | 0 - 3 | Portmore United Portmore United | ||
| 21.10.2024 | | Portmore United Portmore United | 2 - 1 | Chapelton Chapelton | ||
| 07.03.2023 | | Portmore United Portmore United | 0 - 0 | Chapelton Chapelton | ||
| 06.12.2022 | | Chapelton Chapelton | 0 - 1 | Portmore United Portmore United |