Winchester
| Winchester | 1 - 1 | Sita Rangers | 20/06/21 |
| Shooters FC | 6 - 0 | Winchester | 27/06/21 |
| Winchester | 0 - 1 | Murunyu FC | 04/07/21 |
| Dundori Combined | 6 - 0 | Winchester | 11/07/21 |
| Winchester | 3 - 0 | Zanzibar FC | 18/07/21 |
| Shinners FC | 0 - 1 | Winchester | 25/07/21 |
| Winchester | 1 - 2 | Zion FC | 01/08/21 |
| Bahati All Stars | 1 - 2 | Winchester | 08/08/21 |
| Winchester | 0 - 1 | Solai Aqua | 15/08/21 |
| Bahati Arsenal |
-
Suspended |
Winchester | 22/08/21 |
| Winchester |
-
Suspended |
Bahati Arsenal | 19/09/21 |
| Solai Aqua | 1 - 0 | Winchester | 26/09/21 |
| Winchester | 1 - 1 | Bahati All Stars | 03/10/21 |
| Zion FC | 0 - 1 | Winchester | 10/10/21 |
| Winchester | 4 - 3 | Shinners FC | 17/10/21 |
| Zanzibar FC | 1 - 2 | Winchester | 24/10/21 |
| Winchester | 0 - 0 | Dundori Combined | 31/10/21 |
| Murunyu FC | 3 - 2 | Winchester | 07/11/21 |
| Winchester | 0 - 0 | Shooters FC | 14/11/21 |
| Sita Rangers | 0 - 3 | Winchester | 21/11/21 |
| Wanyororo Community |
-
Suspended |
Winchester | 28/11/21 |
