Head to Head
| Club Friendly List | 2018/08/04 14:00 | Winchester City v Weymouth | D | 2-2 |
Home History
| England FA Cup Qualification | 2022/09/02 18:45 | Baffins Milton Rovers v Winchester City | W | 1-5 |
| England Southern Premier League South | 2022/08/29 14:00 | Winchester City v Gosport Borough | L | 0-1 |
| England Southern Premier League South | 2022/08/27 14:00 | Winchester City v Met Police | D | 1-1 |
| England Southern Premier League South | 2022/08/20 14:00 | Winchester City v Truro City | L | 1-3 |
| England Southern Premier League South | 2022/08/16 18:45 | North Leigh v Winchester City | W | 2-4 |
| England Southern Premier League South | 2022/08/13 14:00 | Harrow Borough v Winchester City | D | 1-1 |
| England Southern Premier League South | 2022/08/06 14:00 | Winchester City v Poole Town | L | 0-3 |
| Club Friendly List | 2022/08/02 18:45 | Horsham v Winchester City | L | 2-1 |
Away History
| England National League South | 2022/09/13 18:45 | Bath City v Weymouth | L | 2-1 |
| England National League South | 2022/09/03 14:00 | Weymouth v Hemel Hempstead | D | 0-0 |
| England National League South | 2022/08/29 14:00 | Hungerford Town v Weymouth | D | 1-1 |
| England National League South | 2022/08/27 14:00 | Weymouth v Oxford City | L | 0-2 |
| England National League South | 2022/08/20 14:00 | Chelmsford v Weymouth | L | 3-1 |
| England National League South | 2022/08/16 18:45 | Weymouth v Worthing | L | 0-3 |
| England National League South | 2022/08/13 14:00 | Weymouth v Ebbsfleet United | L | 2-3 |
| England National League South | 2022/08/06 14:00 | Weymouth v Tonbridge Angels | L | 1-3 |