Home History
| England Southern Premier League South | 2023/09/26 18:45 | Winchester City v Basingstoke | W | 2-1 |
| England Southern Premier League South | 2023/09/23 14:00 | Chesham v Winchester City | W | 1-2 |
| England FA Cup Qualification | 2023/09/19 18:45 | Winchester City v Reading City FC | W | 4-1 |
| England FA Cup Qualification | 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 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 |
Away History
| England National League South | 2023/09/23 14:00 | Maidstone Utd v Worthing | W | 4-0 |
| England FA Cup Qualification | 2023/09/16 14:00 | Steyning Town FC v Maidstone Utd | W | 1-4 |
| England National League South | 2023/09/09 14:00 | Chippenham Town v Maidstone Utd | W | 0-2 |
| England National League South | 2023/09/05 18:45 | Maidstone Utd v Aveley | L | 0-1 |
| England National League South | 2023/09/02 14:00 | Weymouth v Maidstone Utd | W | 2-3 |
| England National League South | 2023/08/28 14:00 | Maidstone Utd v Taunton Town | D | 1-1 |
| England National League South | 2023/08/26 14:00 | Hemel Hempstead v Maidstone Utd | D | 1-1 |
| England National League South | 2023/08/19 14:00 | Yeovil v Maidstone Utd | D | 1-1 |