Head to Head
| England Southern Premier League South | 2024/03/16 15:00 | Winchester City v Poole Town | L | 4-0 |
| England Southern Premier League South | 2023/02/14 19:45 | Poole Town v Winchester City | W | 1-0 |
| England FA Trophy | 2022/10/08 14:00 | Winchester City v Poole Town | L | 2-0 |
| England Southern Premier League South | 2022/08/06 14:00 | Winchester City v Poole Town | W | 0-3 |
| UK Friendlies | 2021/07/17 14:00 | Winchester City v Poole Town | W | 2-6 |
Home History
| England Southern Premier League South | 2024/04/06 14:00 | Poole Town v Merthyr Town | L | 1-3 |
| England Southern Premier League South | 2024/04/01 14:00 | Plymouth Parkway v Poole Town | L | 1-0 |
| England Southern Premier League South | 2024/03/29 15:00 | Poole Town v AFC Totton | D | 0-0 |
| England Southern Premier League South | 2024/03/26 19:45 | Poole Town v Hungerford Town | L | 1-2 |
| England Southern Premier League South | 2024/03/23 15:00 | Poole Town v Sholing | L | 0-3 |
| England Southern Premier League South | 2024/03/19 19:45 | Hendon v Poole Town | L | 2-0 |
| England Southern Premier League South | 2024/03/16 15:00 | Winchester City v Poole Town | L | 4-0 |
| England Southern Premier League South | 2024/03/09 15:00 | Poole Town v Walton & Hersham | L | 1-3 |
Away History
| England Southern Premier League South | 2024/04/06 14:00 | Winchester City v Hungerford Town | W | 1-0 |
| England Southern Premier League South | 2024/04/01 14:00 | Gosport Borough v Winchester City | L | 2-1 |
| England Southern Premier League South | 2024/03/30 15:00 | Winchester City v Dorchester | D | 1-1 |
| England Southern Premier League South | 2024/03/23 15:00 | Hendon v Winchester City | L | 2-1 |
| England Southern Premier League South | 2024/03/21 19:45 | Plymouth Parkway v Winchester City | D | 1-1 |
| England Southern Premier League South | 2024/03/16 15:00 | Winchester City v Poole Town | W | 4-0 |
| England Southern Premier League South | 2024/02/24 15:00 | Harrow Borough v Winchester City | W | 1-2 |
| England Southern Premier League South | 2024/02/17 15:00 | Winchester City v Hanwell Town | D | 1-1 |