Home History
| England Southern Premier League South | 2023/08/28 14:00 | Hungerford Town v Didcot Town | D | 2-2 |
| England Southern Premier League South | 2023/08/26 14:00 | Didcot Town v Basingstoke | L | 2-3 |
| England Southern Premier League South | 2023/08/19 14:00 | Tiverton Town v Didcot Town | L | 5-3 |
| England Southern Premier League South | 2023/08/15 18:45 | Didcot Town v Hanwell Town | L | 1-3 |
| England Southern Premier League South | 2023/08/12 14:00 | Bracknell Town v Didcot Town | L | 5-1 |
| England Southern Premier League South | 2023/08/05 14:00 | Didcot Town v Hayes & Yeading | L | 0-1 |
| England Southern League Division One | 2023/05/01 14:00 | Didcot Town v Ware | W | 1-0 |
| England Southern League Division One | 2023/04/05 18:45 | Biggleswade FC v Didcot Town | L | 2-0 |
Away History
| England FA Cup Qualification | 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 |
| England Southern Premier League South | 2023/08/12 14:00 | Winchester City v Sholing | L | 1-3 |
| Club Friendly List | 2023/07/04 18:45 | Badshot v Winchester City | W | 0-6 |
| England Southern Premier League South | 2023/04/22 14:00 | Tiverton Town v Winchester City | W | 2-4 |