Home History
| England FA Cup Qualification | 2024/08/31 14:00 | Chertsey Town v Raynes Park | W | 3-2 |
| England Southern Premier League South | 2024/08/26 14:00 | Walton & Hersham v Chertsey Town | L | 3-2 |
| England Southern Premier League South | 2024/08/24 14:00 | Chertsey Town v Frome Town | D | 1-1 |
| England Southern Premier League South | 2024/08/17 14:00 | Tiverton Town v Chertsey Town | W | 2-3 |
| England Southern Premier League South | 2024/08/14 18:45 | Havant and W v Chertsey Town | L | 3-0 |
| England Southern Premier League South | 2024/08/10 14:00 | Chertsey Town v Hungerford Town | W | 4-1 |
| Club Friendly List | 2024/08/03 14:00 | Chertsey Town v Cray Valley Paper Mills | W | 3-2 |
| Club Friendly List | 2024/07/27 14:00 | Chertsey Town v Hampton & Richmond | L | 0-5 |
Away History
| England FA Cup Qualification | 2024/08/31 14:00 | Tavistock v Winchester City | W | 0-1 |
| England Southern Premier League South | 2024/08/28 18:45 | Winchester City v Dorchester | D | 0-0 |
| England Southern Premier League South | 2024/08/24 14:00 | Plymouth Parkway v Winchester City | W | 0-3 |
| England Southern Premier League South | 2024/08/18 14:00 | Winchester City v Gosport Borough | L | 0-2 |
| England Southern Premier League South | 2024/08/14 18:45 | Winchester City v Wimborne Town | L | 2-4 |
| England Southern Premier League South | 2024/08/10 14:00 | Marlow v Winchester City | D | 1-1 |
| Club Friendly List | 2024/07/16 18:45 | AFC Stoneham v Winchester City | D | 1-1 |
| Club Friendly List | 2024/07/12 18:45 | Ascot Utd v Winchester City | W | 0-1 |