Home History
| Europe Friendlies | 2018/07/28 14:00 | Winchester City v Eastleigh | W | 2-0 |
| England Southern League Division One | 2018/04/12 18:45 | AFC Totton v Winchester City | L | 1-0 |
| England Southern League Division One | 2018/01/31 19:46 | Kidlington v Winchester City | D | 1-1 |
| England Southern League Division One | 2018/01/17 19:45 | Slimbridge v Winchester City | L | 2-0 |
| England FA Cup | 2017/09/02 14:00 | Paulton v Winchester City | L | 1-0 |
| England Southern League Division One | 2017/01/11 18:45 | Evesham United v Winchester City | L | 3-1 |
| England FA Trophy | 2016/11/26 15:00 | Winchester City v Dulwich | L | 0-1 |
| England FA Trophy | 2016/11/12 15:00 | Phoenix Sports v Winchester City | W | 1-3 |
Away History
| Club Friendly List | 2018/07/28 14:00 | Dorchester v Torquay | L | 0-2 |
| Club Friendly List | 2018/07/24 18:45 | Dorchester v Yeovil | L | 0-2 |
| World Club Friendlies | 2018/07/14 14:00 | Saltash Utd v Dorchester | W | 0-2 |
| England Southern League Premier | 2018/04/28 14:00 | Biggleswade Town v Dorchester | D | 1-1 |
| England Southern League Premier | 2018/04/23 18:45 | Hitchin v Dorchester | D | 0-0 |
| England Southern League Premier | 2018/04/21 14:00 | Dorchester v Slough | L | 0-1 |
| England Southern League Premier | 2018/04/17 18:45 | Tiverton Town v Dorchester | D | 0-0 |
| England Southern League Premier | 2018/04/14 14:00 | St Ives Town v Dorchester | W | 1-2 |