Home History
| England Southern League Division One | 2020/10/24 14:00 | Evesham United v Cinderford | D | 1-1 |
| England FA Trophy | 2020/10/17 14:00 | Mangotsfield Utd v Cinderford | W | 1-2 |
| England Southern League Division One | 2020/10/03 14:00 | Cirencester v Cinderford | L | 4-0 |
| England FA Cup | 2020/09/22 18:45 | Cinderford v Wootton Bassett | L | 9-10 |
| Europe Friendlies | 2020/08/22 14:00 | Cinderford v Wantage Town | D | 1-1 |
| 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 |
Away History
| England Southern League Division One | 2020/10/24 14:00 | Highworth Town v Winchester City | L | 1-0 |
| England Southern League Division One | 2020/10/20 18:45 | Winchester City v Bristol Manor Farm | W | 3-2 |
| England FA Trophy | 2020/10/17 14:00 | Highworth Town v Winchester City | L | 2-1 |
| England FA Cup | 2020/10/03 14:00 | Bath City v Winchester City | L | 3-2 |
| England Southern League Division One | 2020/09/29 18:45 | Winchester City v Mangotsfield Utd | W | 5-1 |
| England FA Cup | 2020/09/22 18:45 | Winchester City v Clevedon | W | 3-2 |
| UK Friendlies | 2020/09/05 14:00 | Met Police v Winchester City | L | 4-1 |
| Club Friendly List | 2020/09/01 18:45 | Marlow v Winchester City | W | 1-2 |