Home History
| England Southern League Division One | 2022/01/26 19:30 | Willand Rovers v Highworth Town | L | 0-1 |
| England Southern League Division One | 2021/12/27 13:00 | Willand Rovers v Plymouth Parkway | L | 3-4 |
| England Southern League Division One | 2021/11/17 19:30 | Willand Rovers v Paulton | D | 0-0 |
| England FA Trophy | 2021/11/13 15:00 | Hartley Wintney v Willand Rovers | L | 3-0 |
| England FA Trophy | 2021/10/30 14:00 | Yate Town v Willand Rovers | W | 0-2 |
| England Southern League Cup | 2021/10/13 18:45 | Willand Rovers v Truro City | L | 1-3 |
| England FA Trophy | 2021/10/09 14:00 | Willand Rovers v Mangotsfield Utd | W | 2-1 |
| England Southern League Division One | 2021/09/15 18:30 | Willand Rovers v Bristol Manor Farm | L | 1-2 |
Away History
| England Southern League Division One | 2022/02/12 15:00 | Winchester City v Cinderford | W | 3-1 |
| England Southern League Division One | 2022/02/01 19:45 | Winchester City v Sholing | W | 3-1 |
| England Southern League Division One | 2022/01/07 19:45 | Winchester City v AFC Totton | W | 3-1 |
| England Southern League Division One | 2021/08/18 18:45 | Slimbridge v Winchester City | D | 1-1 |
| Club Friendly List | 2021/08/03 18:45 | Met Police v Winchester City | D | 1-1 |
| UK Friendlies | 2021/07/17 14:00 | Winchester City v Poole Town | L | 2-6 |
| England Southern League Division One | 2020/10/27 19:30 | Cinderford v Winchester City | W | 1-2 |
| England Southern League Division One | 2020/10/24 14:00 | Highworth Town v Winchester City | L | 1-0 |