| 26 Jun 21 | r01        | Arnett GardensArnett Garden | - | UWIUWI |
| 26 Jun 21 | r01        | Mount Pleasant FAMount Pleasan | 0 - 0 | Tivoli GardensTivoli Garden |
| 26 Jun 21 | r01        | CavalierCavalier | 2 - 0 | Humble LionsHumble Lions |
| 27 Jun 21 | r01        | Portmore UnitedPortmore Unit | 2 - 0 | DunbeholdenDunbeholden |
| 28 Jun 21 | r01        | Vere UnitedVere United | 0 - 0 | Molynes UnitedMolynes Unite |
| 28 Jun 21 | r01        | Waterhouse FCWaterhouse FC | 1 - 1 | Harbour ViewHarbour View |
| 16 Jan 22 | r01        | Arnett GardensArnett Garden | 1 - 2 | CavalierCavalier |
| 16 Jan 22 | r01        | Waterhouse FCWaterhouse FC | 2 - 1 | Montego Bay UnitedMontego Bay U |
| 17 Jan 22 | r01        | Vere UnitedVere United | 1 - 2 | DunbeholdenDunbeholden |
| 17 Jan 22 | r01        | Tivoli GardensTivoli Garden | 1 - 1 | Portmore UnitedPortmore Unit |
| 18 Jan 22 | r01        | Harbour ViewHarbour View | 2 - 2 | Molynes UnitedMolynes Unite |
| 18 Jan 22 | r01        | Mount Pleasant FAMount Pleasan | 5 - 1 | Humble LionsHumble Lions |