Home History
| England Southern Premier League South | 2024/11/09 15:00 | Frome Town v Winchester City | W | 0-1 |
| England Southern Premier League South | 2024/11/02 15:00 | Hanwell Town v Winchester City | D | 1-1 |
| England FA Trophy | 2024/10/26 14:00 | Tavistock v Winchester City | W | 0-4 |
| England Southern Premier League South | 2024/10/22 18:45 | Winchester City v Gloucester | L | 2-4 |
| England Southern Premier League South | 2024/10/19 14:00 | Winchester City v Walton & Hersham | W | 2-1 |
| England Southern Premier League South | 2024/10/15 18:45 | Swindon Supermarine v Winchester City | L | 2-0 |
| England Southern Premier League South | 2024/10/12 14:00 | Winchester City v Hungerford Town | D | 2-2 |
| England Southern Premier League South | 2024/10/08 18:45 | Winchester City v Poole Town | D | 1-1 |
Away History
| England FA Trophy | 2024/10/26 14:00 | Dover v Sittingbourne | W | 0-2 |
| England Isthmian Division One South | 2024/10/16 18:30 | Sevenoaks Town v Sittingbourne | D | 1-1 |
| England FA Trophy | 2024/10/05 14:00 | Sittingbourne v Bognor Regis Town | W | 2-1 |
| England Isthmian Division One South | 2024/10/01 18:30 | Burgess Hill Town v Sittingbourne | W | 0-2 |
| England FA Cup Qualification | 2024/09/28 14:00 | Sittingbourne v Plymouth Parkway | L | 0-3 |
| England FA Trophy | 2024/09/21 14:00 | Sittingbourne v Kingstonian | W | 4-1 |
| England FA Cup Qualification | 2024/09/14 11:30 | Lordswood v Sittingbourne | W | 0-1 |
| England FA Cup Qualification | 2024/09/03 18:45 | Dover v Sittingbourne | W | 0-1 |