Head to Head
| England Southern Premier League South | 2023/09/23 14:00 | Chesham v Winchester City | W | 1-2 |
| 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 Southern Premier League South | 2024/01/30 19:45 | Winchester City v Tiverton Town | W | 2-1 |
| England Southern Premier League South | 2024/01/27 15:00 | Basingstoke v Winchester City | W | 0-2 |
| England Southern Premier League South | 2024/01/23 19:45 | Winchester City v Didcot Town | L | 1-2 |
| England Southern Premier League South | 2024/01/20 15:00 | Walton & Hersham v Winchester City | L | 3-1 |
| England Southern Premier League South | 2024/01/13 15:00 | Sholing v Winchester City | L | 5-1 |
| England Southern Premier League South | 2024/01/01 15:00 | Winchester City v Gosport Borough | D | 1-1 |
| England Southern Premier League South | 2023/12/26 15:00 | Salisbury FC v Winchester City | D | 2-2 |
| England Southern Premier League South | 2023/12/23 15:00 | Winchester City v Hayes & Yeading | D | 1-1 |
Away History
| England Southern Premier League South | 2024/01/27 15:00 | Chesham v Walton & Hersham | W | 3-0 |
| England Southern Premier League South | 2024/01/13 15:00 | Hungerford Town v Chesham | W | 0-1 |
| England Southern Premier League South | 2024/01/06 15:00 | Didcot Town v Chesham | D | 1-1 |
| England Southern Premier League South | 2024/01/01 15:00 | Chesham v Harrow Borough | W | 4-0 |
| England Southern Premier League South | 2023/12/26 12:30 | Beaconsfield v Chesham | W | 1-2 |
| England Southern Premier League South | 2023/12/23 15:00 | Chesham v Dorchester | W | 2-0 |
| England Southern Premier League South | 2023/12/16 15:00 | Plymouth Parkway v Chesham | L | 4-0 |
| England Southern Premier League South | 2023/12/05 19:45 | Chesham v Tiverton Town | W | 2-0 |