| 10 Jul 21 | r03        | Portmore UnitedPortmore Unit | 1 - 0 | Molynes UnitedMolynes Unite |
| 10 Jul 21 | r03        | Mount Pleasant FAMount Pleasan | 0 - 2 | Harbour ViewHarbour View |
| 11 Jul 21 | r03        | UWIUWI | - | Tivoli GardensTivoli Garden |
| 11 Jul 21 | r03        | CavalierCavalier | 0 - 1 | DunbeholdenDunbeholden |
| 11 Jul 21 | r03        | Waterhouse FCWaterhouse FC | 0 - 0 | Vere UnitedVere United |
| 12 Jul 21 | r03        | Arnett GardensArnett Garden | 2 - 1 | Humble LionsHumble Lions |
| 02 Oct 21 | r03        | Mount Pleasant FAMount Pleasan | 1 - 1 | Tivoli GardensTivoli Garden |
| 30 Jan 22 | r03        | Waterhouse FCWaterhouse FC | 4 - 1 | DunbeholdenDunbeholden |
| 30 Jan 22 | r03        | CavalierCavalier | 0 - 1 | Portmore UnitedPortmore Unit |
| 31 Jan 22 | r03        | Vere UnitedVere United | 0 - 1 | Mount Pleasant FAMount Pleasan |
| 31 Jan 22 | r03        | Montego Bay UnitedMontego Bay U | 4 - 1 | Molynes UnitedMolynes Unite |
| 01 Feb 22 | r03        | Tivoli GardensTivoli Garden | 1 - 2 | Harbour ViewHarbour View |
| 01 Feb 22 | r03        | Arnett GardensArnett Garden | 2 - 2 | Humble LionsHumble Lions |