Away History
| England Southern Premier League South | 2022/08/29 14:00 | Winchester City v Gosport Borough | L | 0-1 |
| England Southern Premier League South | 2022/08/27 14:00 | Winchester City v Met Police | D | 1-1 |
| England Southern Premier League South | 2022/08/20 14:00 | Winchester City v Truro City | L | 1-3 |
| England Southern Premier League South | 2022/08/16 18:45 | North Leigh v Winchester City | W | 2-4 |
| England Southern Premier League South | 2022/08/13 14:00 | Harrow Borough v Winchester City | D | 1-1 |
| England Southern Premier League South | 2022/08/06 14:00 | Winchester City v Poole Town | L | 0-3 |
| Club Friendly List | 2022/08/02 18:45 | Horsham v Winchester City | L | 2-1 |
| Club Friendly List | 2022/07/26 18:45 | Winchester City v Sholing | D | 2-2 |