Head to Head
| England Southern Premier League South | 2024/08/28 18:45 | Winchester City v Dorchester | D | 0-0 |
| England Southern Premier League South | 2024/03/30 15:00 | Winchester City v Dorchester | D | 1-1 |
| England Southern Premier League South | 2023/08/15 18:45 | Dorchester v Winchester City | L | 0-4 |
| 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 | 2024/12/28 15:00 | Dorchester v Basingstoke | W | 3-2 |
| England Southern Premier League South | 2024/12/26 15:00 | Poole Town v Dorchester | D | 1-1 |
| England Southern Premier League South | 2024/12/21 15:00 | Dorchester v Tiverton Town | W | 5-0 |
| England Southern Premier League South | 2024/12/14 15:00 | Walton & Hersham v Dorchester | D | 2-2 |
| England Southern Premier League South | 2024/12/07 15:00 | Dorchester v Hungerford Town | W | 4-2 |
| England Southern Premier League South | 2024/11/30 15:00 | Wimborne Town v Dorchester | D | 1-1 |
| England Southern Premier League South | 2024/11/23 15:00 | Dorchester v Taunton Town | D | 1-1 |
| England Southern Premier League South | 2024/11/16 15:00 | Dorchester v Merthyr Town | D | 2-2 |
Away History
| England Southern Premier League South | 2024/12/28 15:00 | Gosport Borough v Winchester City | W | 1-3 |
| England Southern Premier League South | 2024/12/26 13:00 | Winchester City v AFC Totton | L | 1-4 |
| England Southern Premier League South | 2024/12/21 15:00 | Wimborne Town v Winchester City | W | 2-4 |
| England Southern Premier League South | 2024/12/17 19:45 | Winchester City v Basingstoke | L | 2-4 |
| England Southern Premier League South | 2024/12/14 15:00 | Winchester City v Bracknell Town | D | 0-0 |
| England Southern Premier League South | 2024/11/30 15:00 | Sholing v Winchester City | W | 0-1 |
| England Southern Premier League South | 2024/11/23 15:00 | Winchester City v Havant and W | L | 1-3 |
| England FA Trophy | 2024/11/16 15:00 | Winchester City v Sittingbourne | L | 5-6 |