| 2021-01-21 18:00:00January 21, 2021 | Promex Harlem United SC vs East Central FC | 2 - 1 | Nations Cup | 2021 | | Recap | - |
| 2021-01-21 18:00:00January 21, 2021 | Mahaut Soca Strikers FC vs Police SC | 2 - 0 | Nations Cup | 2021 | | Recap | - |
| 2021-01-22 18:00:00January 22, 2021 | Sagicor South East FC vs ACS Pottersville Tarish United FC | 3 - 2 | Nations Cup | 2021 | | Recap | - |
| 2021-01-22 18:00:00January 22, 2021 | Middleham United vs Exodus FC | 0 - 2 | Nations Cup | 2021 | | Recap | - |
| 2021-01-23 15:30:00January 23, 2021 | LA Enterprise Bombers FC vs Petro Caribe Pointe Michel | 0 - 2 | Nations Cup | 2021 | | Recap | - |
| 2021-01-23 16:00:00January 23, 2021 | CCCUL Dublanc FC vs RC Doctors | 9 - 0 | Nations Cup | 2021 | | Recap | - |
| 2021-01-24 15:30:00January 24, 2021 | Happi Bath Estate FC vs LA Starz FC | 6 - 2 | Nations Cup | 2021 | | Recap | - |
| 2021-01-24 16:00:00January 24, 2021 | We United FC vs Busta Warner FC | 16:00:004:00 pm | Nations Cup | 2021 | | Recap | - |
| 2021-01-27 18:00:00January 27, 2021 | Promex Harlem United SC vs Mahaut Soca Strikers | 3 - 0 | Nations Cup | 2021 | | Recap | - |
| 2021-01-28 18:00:00January 28, 2021 | Sagicor South East FC vs Exodus FC | 6 - 0 | Nations Cup | 2021 | | Recap | - |
| 2021-01-28 19:00:00January 28, 2021 | Promex Harlem United SC vs Sagicor South East FC | 1 - 5 | Nations Cup | 2021 | | Recap | - |
| 2021-01-29 18:00:00January 29, 2021 | Petro Caribe Pointe Michel vs CCCUL Dublanc FC | 0 - 3 | Nations Cup | 2021 | | Recap | - |
| 2021-01-31 18:00:00January 31, 2021 | We United FC vs Happi Bath Estate FC | 5 - 6 | Nations Cup | 2021 | | Recap | - |
| 2021-02-07 15:30:00February 7, 2021 | CCCUL Dublanc FC vs Happi Bath Estate FC | 0 - 1 | Nations Cup | 2021 | | Recap | - |
| 2021-02-13 15:30:00February 13, 2021 | Sagicor South East FC vs Happi Bath Estate FC | 2 - 1 | Nations Cup | 2021 | | Recap | - |
