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 |
Home History
| 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 |
| England Southern Premier League South | 2024/02/06 19:45 | Winchester City v Swindon Supermarine | D | 2-2 |
| England Southern Premier League South | 2024/02/03 15:00 | Winchester City v Chesham | L | 0-3 |
| England Southern Premier League South | 2024/01/30 19:45 | Winchester City v Tiverton Town | W | 2-1 |
| England Southern Premier League South | 2024/01/27 15:00 | Basingstoke v Winchester City | W | 0-2 |
| England Southern Premier League South | 2024/01/23 19:45 | Winchester City v Didcot Town | L | 1-2 |
| England Southern Premier League South | 2024/01/20 15:00 | Walton & Hersham v Winchester City | L | 3-1 |
Away History
| England Southern Premier League South | 2024/03/09 15:00 | Poole Town v Walton & Hersham | L | 1-3 |
| England Southern Premier League South | 2024/03/06 19:45 | Gosport Borough v Poole Town | W | 1-2 |
| England Southern Premier League South | 2024/02/24 15:00 | Chesham v Poole Town | L | 3-1 |
| England Southern Premier League South | 2024/02/17 15:00 | Poole Town v Basingstoke | L | 0-1 |
| England Southern Premier League South | 2024/02/10 15:00 | Salisbury FC v Poole Town | L | 2-0 |
| England Southern Premier League South | 2024/02/06 19:45 | Poole Town v Hayes & Yeading | L | 0-2 |
| England Southern Premier League South | 2024/02/03 15:00 | Poole Town v Hanwell Town | L | 0-3 |
| England Southern Premier League South | 2024/01/30 19:45 | Poole Town v Salisbury FC | L | 4-5 |