Head to Head
| England Southern Premier League South | 2023/03/18 15:00 | Chesham v Winchester City | D | 1-1 |
| England Southern Premier League South | 2022/10/15 14:00 | Winchester City v Chesham | D | 1-1 |
Home History
| England FA Cup | 2023/09/16 14:00 | Farnham v Chesham | W | 1-2 |
| England Southern Premier League South | 2023/09/09 14:00 | Merthyr Town v Chesham | W | 1-3 |
| England Southern Premier League South | 2023/09/05 18:45 | Hanwell Town v Chesham | W | 0-3 |
| England FA Cup | 2023/09/02 14:00 | Walton & Hersham v Chesham | W | 1-3 |
| England Southern Premier League South | 2023/08/28 14:00 | Chesham v Beaconsfield | W | 3-0 |
| England Southern Premier League South | 2023/08/26 14:00 | Dorchester v Chesham | W | 0-2 |
| England Southern Premier League South | 2023/08/19 14:00 | Chesham v Plymouth Parkway | W | 4-3 |
| England Southern Premier League South | 2023/08/15 18:45 | Hayes & Yeading v Chesham | W | 1-2 |
Away History
| England FA Cup | 2023/09/19 18:45 | Winchester City v Reading City FC | W | 4-1 |
| England FA Cup | 2023/09/16 14:00 | Reading City FC v Winchester City | D | 1-1 |
| England Southern Premier League South | 2023/09/09 14:00 | Didcot Town v Winchester City | L | 1-0 |
| England FA Cup | 2023/09/02 14:00 | Winchester City v Evesham United | W | 3-2 |
| England Southern Premier League South | 2023/08/28 14:00 | Winchester City v Salisbury FC | D | 1-1 |
| England Southern Premier League South | 2023/08/26 14:00 | Hayes & Yeading v Winchester City | W | 1-3 |
| England Southern Premier League South | 2023/08/19 14:00 | Winchester City v AFC Totton | L | 0-6 |
| England Southern Premier League South | 2023/08/15 18:45 | Dorchester v Winchester City | W | 0-4 |