Head to Head
| England Southern Premier League South | 2023/02/14 19:45 | Poole Town v Winchester City | L | 1-0 |
| England FA Trophy | 2022/10/08 14:00 | Winchester City v Poole Town | W | 2-0 |
| 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 |