Home History
| 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 |
| 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 |
Away History
| England FA Trophy | 2020/12/19 15:00 | Maidstone Utd v Poole Town | L | 2-0 |
| England FA Trophy | 2020/12/08 19:45 | Poole Town v Willand Rovers | W | 3-1 |
| England FA Trophy | 2020/10/31 15:00 | Hartley Wintney v Poole Town | W | 1-4 |
| England Southern Premier League South | 2020/10/27 19:45 | Poole Town v Gosport Borough | W | 1-0 |
| England Southern Premier League South | 2020/10/24 14:00 | Yate Town v Poole Town | W | 2-6 |
| England Southern Premier League South | 2020/10/17 14:00 | Poole Town v Hendon | W | 1-0 |
| England Southern Premier League South | 2020/10/10 14:00 | Salisbury FC v Poole Town | D | 2-2 |
| England Southern Premier League South | 2020/10/06 18:45 | Poole Town v Truro City | W | 2-1 |