Home History
| England FA Cup | 2020/09/22 18:30 | Cowes Sports v Weston Super Mare | L | 0-5 |
Away History
| England Southern Premier League South | 2024/04/27 14:00 | Swindon Supermarine v Winchester City | L | 3-0 |
| England Southern Premier League South | 2024/04/20 14:00 | Winchester City v Beaconsfield | W | 1-0 |
| England Southern Premier League South | 2024/04/18 18:45 | Tiverton Town v Winchester City | L | 2-0 |
| England Southern Premier League South | 2024/04/16 18:45 | Winchester City v Merthyr Town | W | 2-0 |
| England Southern Premier League South | 2024/04/13 14:00 | Bracknell Town v Winchester City | L | 3-1 |
| England Southern Premier League South | 2024/04/09 19:00 | Poole Town v Winchester City | L | 2-1 |
| England Southern Premier League South | 2024/04/06 14:00 | Winchester City v Hungerford Town | W | 1-0 |
| England Southern Premier League South | 2024/04/01 14:00 | Gosport Borough v Winchester City | L | 2-1 |