Head to Head
| 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 | 2023/02/11 15:00 | Yate Town v Poole Town | W | 2-3 |
| England Southern Premier League South | 2023/02/07 19:45 | Poole Town v Swindon Supermarine | D | 2-2 |
| England Southern Premier League South | 2023/02/04 15:00 | Poole Town v Gosport Borough | D | 1-1 |
| England Southern Premier League South | 2023/01/28 15:00 | Plymouth Parkway v Poole Town | L | 4-0 |
| England Southern Premier League South | 2023/01/02 15:00 | Salisbury FC v Poole Town | W | 1-3 |
| England Southern Premier League South | 2022/12/26 13:00 | Poole Town v Dorchester | W | 3-0 |
| England Southern Premier League South | 2022/12/03 15:00 | North Leigh v Poole Town | W | 0-4 |
| England Southern Premier League South | 2022/11/26 15:00 | Poole Town v Hanwell Town | W | 3-2 |
Away History
| England Southern Premier League South | 2023/02/11 15:00 | Hendon v Winchester City | W | 0-2 |
| England Southern Premier League South | 2023/02/07 19:45 | Winchester City v Harrow Borough | D | 0-0 |
| England Southern Premier League South | 2023/02/04 15:00 | Winchester City v Merthyr Town | D | 2-2 |
| England Southern Premier League South | 2023/01/28 15:00 | Bracknell Town v Winchester City | L | 3-1 |
| England Southern Premier League South | 2023/01/14 15:00 | Dorchester v Winchester City | L | 2-1 |
| England Southern Premier League South | 2023/01/07 15:00 | Met Police v Winchester City | L | 2-1 |
| England Southern Premier League South | 2023/01/02 15:00 | Gosport Borough v Winchester City | D | 2-2 |
| England Southern Premier League South | 2022/12/26 15:00 | Winchester City v Salisbury FC | L | 0-1 |