Head to Head
| England Southern Premier League South | 2024/09/07 14:00 | Chertsey Town v Winchester City | D | 3-3 |
Home History
| England Southern Premier League South | 2025/02/01 15:00 | Walton & Hersham v Winchester City | L | 4-2 |
| England Southern Premier League South | 2025/01/25 15:00 | Winchester City v Swindon Supermarine | W | 1-0 |
| England Southern Premier League South | 2025/01/18 15:00 | Winchester City v Frome Town | L | 1-3 |
| England Southern Premier League South | 2025/01/11 15:00 | Basingstoke v Winchester City | L | 2-0 |
| England Southern Premier League South | 2025/01/04 15:00 | Winchester City v Marlow | W | 3-1 |
| England Southern Premier League South | 2025/01/01 15:00 | Dorchester v Winchester City | L | 1-0 |
| England Southern Premier League South | 2024/12/28 15:00 | Gosport Borough v Winchester City | W | 1-3 |
| England Southern Premier League South | 2024/12/26 13:00 | Winchester City v AFC Totton | L | 1-4 |
Away History
| England Southern Premier League South | 2025/02/01 15:00 | Plymouth Parkway v Chertsey Town | L | 2-1 |
| England Southern Premier League South | 2025/01/25 15:00 | Chertsey Town v Marlow | L | 2-5 |
| England Southern Premier League South | 2025/01/18 15:00 | Swindon Supermarine v Chertsey Town | L | 1-0 |
| England Southern Premier League South | 2025/01/14 19:45 | Chertsey Town v Poole Town | W | 2-1 |
| England FA Trophy | 2025/01/04 15:00 | Aldershot v Chertsey Town | L | 8-0 |
| England Southern Premier League South | 2024/12/28 15:00 | Chertsey Town v Tiverton Town | D | 2-2 |
| England Southern Premier League South | 2024/12/26 15:00 | Hanwell Town v Chertsey Town | W | 1-2 |
| England Southern Premier League South | 2024/12/21 15:00 | Chertsey Town v Havant and W | L | 0-4 |