Head to Head
| England FA Cup Qualification | 2022/09/17 14:00 | Winchester City v Weymouth | L | 1-3 |
| Club Friendly List | 2018/08/04 14:00 | Winchester City v Weymouth | D | 2-2 |
Home History
| England Southern Premier League South | 2024/09/24 18:45 | Merthyr Town v Winchester City | L | 3-1 |
| England Southern Premier League South | 2024/09/21 14:00 | Tiverton Town v Winchester City | L | 2-1 |
| England FA Cup Qualification | 2024/09/17 18:45 | Hungerford Town v Winchester City | W | 0-1 |
| England FA Cup Qualification | 2024/09/14 14:00 | Winchester City v Hungerford Town | D | 1-1 |
| England Southern Premier League South | 2024/09/07 14:00 | Chertsey Town v Winchester City | D | 3-3 |
| England FA Cup Qualification | 2024/08/31 14:00 | Tavistock v Winchester City | W | 0-1 |
| England Southern Premier League South | 2024/08/28 18:45 | Winchester City v Dorchester | D | 0-0 |
| England Southern Premier League South | 2024/08/24 14:00 | Plymouth Parkway v Winchester City | W | 0-3 |
Away History
| England National League South | 2024/09/21 14:00 | Weymouth v Worthing | D | 1-1 |
| England FA Cup Qualification | 2024/09/14 14:00 | Sholing v Weymouth | W | 1-4 |
| England National League South | 2024/09/07 14:00 | Dorking Wanderers v Weymouth | W | 1-2 |
| England National League South | 2024/09/03 18:45 | Weymouth v Hampton & Richmond | L | 0-1 |
| England National League South | 2024/08/31 17:50 | Slough v Weymouth | L | 1-0 |
| England National League South | 2024/08/26 14:00 | Weymouth v Eastbourne Borough | L | 0-1 |
| England National League South | 2024/08/24 14:00 | Boreham Wood v Weymouth | L | 3-0 |
| England National League South | 2024/08/20 18:45 | Weymouth v Chippenham Town | L | 0-2 |