Head to Head
| England Southern Premier League South | 2023/01/14 15:00 | Dorchester v Winchester City | W | 2-1 |
| 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 | 2023/04/22 14:00 | Met Police v Dorchester | W | 1-3 |
| England Southern Premier League South | 2023/04/15 14:00 | Dorchester v Hendon | W | 3-2 |
| England Southern Premier League South | 2023/04/10 14:00 | Dorchester v Poole Town | L | 1-6 |
| England Southern Premier League South | 2023/04/07 14:00 | Chesham v Dorchester | L | 2-0 |
| England Southern Premier League South | 2023/04/01 14:00 | Salisbury FC v Dorchester | D | 2-2 |
| England Southern Premier League South | 2023/03/28 18:45 | Harrow Borough v Dorchester | W | 1-2 |
| England Southern Premier League South | 2023/03/25 15:00 | Dorchester v Merthyr Town | L | 0-2 |
| England Southern Premier League South | 2023/03/18 15:00 | Hayes & Yeading v Dorchester | L | 4-0 |
Away History
| England Southern Premier League South | 2023/04/22 14:00 | Tiverton Town v Winchester City | W | 2-4 |
| England Southern Premier League South | 2023/04/18 18:45 | Plymouth Parkway v Winchester City | L | 1-0 |
| England Southern Premier League South | 2023/04/15 14:00 | Winchester City v Hanwell Town | L | 0-3 |
| England Southern Premier League South | 2023/04/10 14:00 | Salisbury FC v Winchester City | W | 1-2 |
| England Southern Premier League South | 2023/04/08 14:00 | Winchester City v Hayes & Yeading | W | 3-0 |
| England Southern Premier League South | 2023/04/04 19:00 | Weston Super Mare v Winchester City | L | 3-1 |
| England Southern Premier League South | 2023/03/25 15:00 | Winchester City v Beaconsfield | W | 4-0 |
| England Southern Premier League South | 2023/03/18 15:00 | Chesham v Winchester City | D | 1-1 |