| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 03.07.2021 | Matchday 2 | Matchday 2 | A | ![]() | Molynes United | -:-dnp | |
| 11.07.2021 | Matchday 3 | Matchday 3 | H | ![]() | Tivoli Gardens | -:-dnp | |
| 19.07.2021 | Matchday 4 | Matchday 4 | H | ![]() | Waterhouse | -:-dnp | |
| 24.07.2021 | Matchday 5 | Matchday 5 | A | ![]() | Cavalier | -:-dnp | |
| 02.08.2021 | Matchday 6 | Matchday 6 | H | ![]() | Mount Pleasant Academy | -:-dnp | |
| 07.08.2021 | Matchday 7 | Matchday 7 | A | ![]() | Dunbeholden FC | -:-dnp | |
| 16.08.2021 | Matchday 8 | Matchday 8 | H | ![]() | Vere United | -:-dnp | |
| 23.08.2021 | Matchday 9 | Matchday 9 | A | ![]() | Portmore Utd. | -:-dnp | |
| 30.08.2021 | Matchday 10 | Matchday 10 | H | ![]() | Harbour View | -:-dnp | |
| 05.09.2021 | Matchday 11 | Matchday 11 | A | ![]() | Humble Lions | -:-dnp | |
UWI Pelicans










