| 2021-05-27 20:15:56May 27, 2021 | RAMS Village Superstars 
 St. Peters
| 20:15:568:15 pm | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-27 18:00:02May 27, 2021 | SOL Island Auto Conaree 
 SLH Horsfords St. Pauls United
| 18:00:026:00 pm | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-23 19:30:48May 23, 2021 | St. Peters
SLH Horsfords St. Pauls United
| 0 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-23 17:15:57May 23, 2021 | H.E. Garden Hotspurs 
 FLOW 4G Cayon Rockets
| 0 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-23 17:15:49May 23, 2021 | T.G.E Dieppe Bay Eagles 
 Trafalgar Southstars
| 2 - 0 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-22 20:30:57May 22, 2021 | S-krave Newtown United 
RAMS Village Superstars
| 0 - 1 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-22 18:15:47May 22, 2021 | SOL Island Auto Conaree
 MFCR United Old Road Jets
| 1 - 1 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-22 16:00:19May 22, 2021 | Fast Cash Saddlers United 
 Hotspring Bath United
| 16:00:194:00 pm | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-20 20:30:27May 20, 2021 | Newton Ground Ballers 
 Sandy Point
| 0 - 3 | | Recap |
| 2021-05-20 18:00:07May 20, 2021 | Conaree Fireballs International
 KFC Trinity/Challengers United
| 4 - 0 | | Recap |
| 2021-05-18 20:30:13May 18, 2021 | ELCO Ltd Security Forces United 
 Molineaux
| 11 - 1 | | Recap |
| 2021-05-18 18:00:13May 18, 2021 | Rivers of Living Water
 Mantab
| 0 - 1 | | Recap |
| 2021-05-16 19:30:59May 16, 2021 | SOL Island Auto Conaree
H.E. Garden Hotspurs
| 2 - 1 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-16 17:15:58May 16, 2021 | Fast Cash Saddlers United
RAMS Village Superstars
| 0 - 1 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-16 15:00:11May 16, 2021 | Hotspring Bath United
St. Peters
| 0 - 2 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-15 20:30:19May 15, 2021 | MFCR United Old Road Jets
S-krave Newtown United
| 2 - 2 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-15 18:15:25May 15, 2021 | T.G.E Dieppe Bay Eagles
SLH Horsfords St. Pauls United
| 0 - 7 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-15 16:00:50May 15, 2021 | Trafalgar Southstars
FLOW 4G Cayon Rockets
| 1 - 6 | Warner ParkLozac Rd, Basseterre, Saint Kitts and Nevis | Recap |
| 2021-05-15 15:00:10May 15, 2021 | ELCO Ltd Security Forces United
Hardtimes United
| 3 - 0 | | Recap |
| 2021-05-13 20:30:58May 13, 2021 | KFC Trinity/Challengers United
Sandy Point
| 1 - 5 | Sandy Point Playing Field | Recap |
