Head to Head
| England Southern Premier League South | 2022/08/06 14:00 | Winchester City v Poole Town | L | 0-3 |
| UK Friendlies | 2021/07/17 14:00 | Winchester City v Poole Town | L | 2-6 |
Home History
| England Southern Premier League South | 2022/09/27 18:45 | Merthyr Town v Winchester City | L | 5-2 |
| England Southern Premier League South | 2022/09/24 14:00 | Winchester City v Hendon | D | 1-1 |
| England FA Cup | 2022/09/17 14:00 | Winchester City v Weymouth | L | 1-3 |
| England FA Cup Qualification | 2022/09/02 18:45 | Baffins Milton Rovers v Winchester City | W | 1-5 |
| England Southern Premier League South | 2022/08/29 14:00 | Winchester City v Gosport Borough | L | 0-1 |
| England Southern Premier League South | 2022/08/27 14:00 | Winchester City v Met Police | D | 1-1 |
| England Southern Premier League South | 2022/08/20 14:00 | Winchester City v Truro City | L | 1-3 |
| England Southern Premier League South | 2022/08/16 18:45 | North Leigh v Winchester City | W | 2-4 |
Away History
| England Southern Premier League South | 2022/10/01 14:00 | Beaconsfield v Poole Town | W | 0-2 |
| England Southern Premier League South | 2022/09/28 18:45 | Gosport Borough v Poole Town | W | 1-2 |
| England Southern Premier League South | 2022/09/24 14:00 | Poole Town v Yate Town | W | 5-0 |
| England FA Cup | 2022/09/03 14:00 | Poole Town v Salisbury FC | L | 0-2 |
| England Southern Premier League South | 2022/08/29 14:00 | Poole Town v Salisbury FC | L | 1-2 |
| England Southern Premier League South | 2022/08/27 14:00 | Merthyr Town v Poole Town | W | 1-2 |
| England Southern Premier League South | 2022/08/20 14:00 | Poole Town v Weston Super Mare | L | 1-3 |
| England Southern Premier League South | 2022/08/17 18:45 | Truro City v Poole Town | D | 1-1 |
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