Head to Head
| England Southern Premier League South | 2022/11/26 15:00 | Winchester City v Dorchester | D | 1-1 |
| Club Friendly List | 2018/08/01 18:45 | Winchester City v Dorchester | L | 5-1 |
Home History
| England Southern Premier League South | 2023/01/07 15:00 | Hartley Wintney v Dorchester | W | 2-4 |
| England Southern Premier League South | 2023/01/02 15:00 | Dorchester v Yate Town | W | 2-0 |
| England Southern Premier League South | 2022/12/26 13:00 | Poole Town v Dorchester | L | 3-0 |
| England Southern Premier League South | 2022/12/17 15:00 | Dorchester v Truro City | W | 1-0 |
| England Southern Premier League South | 2022/12/03 15:00 | Dorchester v Chesham | L | 1-3 |
| England Southern Premier League South | 2022/11/26 15:00 | Winchester City v Dorchester | D | 1-1 |
| England Southern Premier League South | 2022/11/12 15:00 | Hendon v Dorchester | D | 0-0 |
| England Southern Premier League South | 2022/11/05 15:00 | Dorchester v Met Police | W | 1-0 |
Away History
| 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 |
| England Southern Premier League South | 2022/12/03 15:00 | Hayes & Yeading v Winchester City | L | 4-0 |
| England Southern Premier League South | 2022/11/26 15:00 | Winchester City v Dorchester | D | 1-1 |
| England Southern Premier League South | 2022/11/22 19:45 | Winchester City v North Leigh | D | 2-2 |
| England Southern Premier League South | 2022/11/19 15:00 | Truro City v Winchester City | L | 3-0 |
| England Southern Premier League South | 2022/11/12 15:00 | Hanwell Town v Winchester City | W | 1-2 |