Home History
| England Southern League Division One | 2020/10/10 14:00 | Melksham Town v Highworth Town | W | 0-1 |
| England Southern League Division One | 2020/10/07 18:45 | Highworth Town v Slimbridge | D | 2-2 |
| England Southern League Division One | 2020/09/26 14:00 | Bristol Manor Farm v Highworth Town | L | 3-2 |
| England FA Cup Qualification | 2020/09/23 18:45 | Highworth Town v Melksham Town | L | 5-6 |
| England Southern League Division One | 2020/09/19 14:00 | Highworth Town v Willand Rovers | W | 1-0 |
| England Southern League Division One | 2020/02/12 19:46 | Highworth Town v AFC Totton | L | 1-2 |
| England Southern League Cup | 2019/10/02 18:45 | Highworth Town v Swindon Supermarine | L | 0-4 |
| England FA Cup Qualification | 2019/09/21 14:00 | Tavistock v Highworth Town | L | 4-0 |
Away History
| 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 |
| 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 |