| Date | Home | Result | Away | |
| 27-10-20 | Cinderford Town | 1 - 2 |
Winchester City | |
| 24-10-20 | Highworth Town FC | 1 - 0 |
Winchester City | |
| 20-10-20 | Winchester City | 3 - 2 |
Bristol Manor Farm | |
| 10-10-20 | Winchester City | 0 - 1 |
Evesham United | |
| 06-10-20 | AFC Totton | 1 - 2 |
Winchester City | |
| 29-09-20 | Winchester City | 5 - 1 |
Mangotsfield United | |
| 19-09-20 | Melksham Town FC | 1 - 2 |
Winchester City |