 University of the West Indies Football Club |
| 12-Jan-2020 | NPL (22) | UWI | 0-0 | Dunbeholden |
| 19-Jan-2020 | NPL (23) | Tivoli Gardens | 1-0 | UWI |
| 26-Jan-2020 | NPL (24) | UWI | 1-1 | Molynes United |
| 30-Jan-2020 | NPL (25) | UWI | 1-3 | Arnett Gardens |
| 16-Feb-2020 | NPL (26) | Mount Pleasant | 3-0 | UWI |
| 23-Feb-2020 | NPL (27) | UWI | 0-3 | Cavalier |
| 02-Mar-2020 | NPL (28) | Waterhouse | 3-1 | UWI |
| 08-Mar-2020 | NPL (29) | UWI | 1-3 | Portmore United |
