Head to Head
| 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 | W | 0-4 |
| England Southern Premier League South | 2023/01/14 15:00 | Dorchester v Winchester City | L | 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 | W | 5-1 |
Home History
| England Southern Premier League South | 2024/08/24 14:00 | Plymouth Parkway v Winchester City | W | 0-3 |
| England Southern Premier League South | 2024/08/18 14:00 | Winchester City v Gosport Borough | L | 0-2 |
| England Southern Premier League South | 2024/08/14 18:45 | Winchester City v Wimborne Town | L | 2-4 |
| England Southern Premier League South | 2024/08/10 14:00 | Marlow v Winchester City | D | 1-1 |
| Club Friendly List | 2024/07/16 18:45 | AFC Stoneham v Winchester City | D | 1-1 |
| Club Friendly List | 2024/07/12 18:45 | Ascot Utd v Winchester City | W | 0-1 |
| England Southern Premier League South | 2024/04/27 14:00 | Swindon Supermarine v Winchester City | L | 3-0 |
| England Southern Premier League South | 2024/04/20 14:00 | Winchester City v Beaconsfield | W | 1-0 |
Away History
| England Southern Premier League South | 2024/08/24 14:00 | Dorchester v Gloucester | W | 1-0 |
| England Southern Premier League South | 2024/08/17 14:00 | Basingstoke v Dorchester | L | 2-0 |
| England Southern Premier League South | 2024/08/13 18:45 | Tiverton Town v Dorchester | D | 1-1 |
| England Southern Premier League South | 2024/08/10 14:00 | Dorchester v Havant and W | D | 1-1 |
| Club Friendly List | 2024/08/03 14:00 | Weymouth v Dorchester | W | 0-2 |
| England Southern Premier League South | 2024/04/27 14:00 | Dorchester v AFC Totton | L | 0-4 |
| England Southern Premier League South | 2024/04/20 14:00 | Basingstoke v Dorchester | L | 3-1 |
| England Southern Premier League South | 2024/04/16 18:45 | Tiverton Town v Dorchester | W | 0-2 |