Home History
| England Southern League Division One | 2020/01/28 19:39 | Cinderford v Bideford | L | 1-2 |
| England FA Trophy | 2019/11/23 15:00 | Havant and W v Cinderford | L | 3-1 |
| England Southern League Cup | 2019/11/19 19:45 | Swindon Supermarine v Cinderford | L | 6-0 |
| England FA Trophy | 2019/11/09 15:00 | Cinderford v Potters Bar Town | W | 1-0 |
| England FA Trophy | 2019/11/05 19:45 | Merthyr Town v Cinderford | D | 4-4 |
| England Southern League Cup | 2019/10/01 18:44 | Merthyr Town v Cinderford | W | 1-2 |
| England FA Cup Qualification | 2019/09/21 14:00 | Brackley v Cinderford | L | 4-0 |
| England FA Cup | 2019/09/07 14:00 | Cinderford v Bideford | W | 5-3 |
Away History
| England FA Trophy | 2019/10/22 18:45 | Thame Utd v Winchester City | L | 5-3 |
| England FA Trophy | 2019/10/15 18:48 | Winchester City v Thame Utd | D | 3-3 |
| England FA Cup Qualification | 2019/09/07 14:00 | Winchester City v Taunton Town | L | 0-3 |
| England Southern League Division One | 2019/08/20 18:46 | Winchester City v AFC Totton | W | 2-1 |
| UK Friendlies | 2019/07/16 18:45 | Hamworthy Utd v Winchester City | W | 0-2 |
| UK Friendlies | 2019/07/09 18:42 | Ringwood Town v Winchester City | W | 2-3 |
| England Southern League Division One | 2019/04/09 18:46 | Winchester City v AFC Totton | W | 2-1 |
| England FA Cup Qualification | 2018/10/20 14:00 | Torquay v Winchester City | L | 4-1 |