| 2020-12-16 19:00:36December 16, 2020 | SLH Horsfords St. Pauls United 
 RAMS Village Superstars
| 2 - 1 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-14 17:30:40December 14, 2020 | Rams Village Superstars (F)
 Bath United (F)
| 3 - 0 | | Recap |
| 2020-12-12 19:00:18December 12, 2020 | SLH Horsfords St. Pauls United
RAMS Village Superstars
| 2 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-12 15:00:01December 12, 2020 | Rams Village Superstars (F)
 National U-15 (F)
| 2 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-09 20:00:39December 9, 2020 | RAMS Village Superstars
SLH Horsfords St. Pauls United
| 0 - 3 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-09 18:00:40December 9, 2020 | SOL Island Auto Conaree 
 St. Peters
| 3 - 3 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-08 19:00:47December 8, 2020 | FLOW 4G Cayon Rockets 
 H.E. Garden Hotspurs
| 0 - 2 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-06 18:00:53December 6, 2020 | RAMS Village Superstars
SOL Island Auto Conaree
| 2 - 1 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-06 15:00:36December 6, 2020 | Flow 4G Cayon Rockets (F)
Rams Village Superstars (F)
| 0 - 2 | | Recap |
| 2020-12-06 15:00:27December 6, 2020 | S-Krave Newtown United (F) 
Flow 4G Cayon Rockets (F)
| 1 - 0 | Newtown Playing FieldBasseterre, Saint George Basseterre, Saint Kitts, 00265, Saint Kitts and Nevis | Recap |
| 2020-12-06 14:00:29December 6, 2020 | National U-15 (F)
Bath United (F)
| 3 - 0 | | Recap |
| 2020-12-05 19:00:57December 5, 2020 | SLH Horsfords St. Pauls United
H.E. Garden Hotspurs
| 2 - 1 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-05 17:00:51December 5, 2020 | FLOW 4G Cayon Rockets
St. Peters
| 1 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-02 20:00:06December 2, 2020 | RAMS Village Superstars
FLOW 4G Cayon Rockets
| 0 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-02 18:00:09December 2, 2020 | St. Peters
H.E. Garden Hotspurs
| 4 - 3 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-12-01 20:00:36December 1, 2020 | SLH Horsfords St. Pauls United
SOL Island Auto Conaree
| 3 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-11-30 20:00:26November 30, 2020 | Bath United
 T.G.E Dieppe Bay Eagles
| 1 - 3 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-11-30 18:00:34November 30, 2020 | KFC Trinity/Challengers United 
 Davis Construction Lodge Patriots
| 2 - 1 | | Recap |
| 2020-11-29 19:00:42November 29, 2020 | RAMS Village Superstars
St. Peters
| 3 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2020-11-29 15:00:42November 29, 2020 | Rams Village Superstars (F)
S-Krave Newtown United (F)
| 0 - 3 | | Recap |
