Home History
| England Southern Premier League South | 2022/10/11 18:45 | Winchester City v Hartley Wintney | W | 2-1 |
| England FA Trophy | 2022/10/08 14:00 | Winchester City v Poole Town | W | 2-0 |
| England Southern Premier League South | 2022/09/27 18:45 | Merthyr Town v Winchester City | L | 5-2 |
| England Southern Premier League South | 2022/09/24 14:00 | Winchester City v Hendon | D | 1-1 |
| England FA Cup | 2022/09/17 14:00 | Winchester City v Weymouth | L | 1-3 |
| England FA Cup Qualification | 2022/09/02 18:45 | Baffins Milton Rovers v Winchester City | W | 1-5 |
| 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 |
Away History
| England Southern Premier League South | 2022/10/11 18:45 | Harrow Borough v Chesham | L | 2-1 |
| England FA Trophy | 2022/10/08 14:00 | Enfield Town v Chesham | W | 0-4 |
| England Southern Premier League South | 2022/10/01 14:00 | Chesham v Tiverton Town | W | 3-0 |
| England Southern Premier League South | 2022/09/27 18:45 | Hendon v Chesham | D | 0-0 |
| England FA Cup Qualification | 2022/09/20 18:30 | Bracknell Town v Chesham | L | 3-0 |
| England FA Cup Qualification | 2022/09/16 18:45 | Chesham v Bracknell Town | D | 2-2 |
| England Southern Premier League South | 2022/09/13 18:45 | Chesham v Beaconsfield | W | 4-2 |
| England FA Cup | 2022/09/03 14:00 | Chesham v Peacehaven & Telscombe | W | 5-2 |