Home History
| Club Friendly List | 2018/08/01 18:45 | Winchester City v Dorchester | W | 5-1 |
| 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 |
Away History
| Europe Friendlies | 2018/07/28 14:00 | Weymouth v Bath City | L | 1-2 |
| Europe Friendlies | 2018/07/21 14:00 | Hamworthy Utd v Weymouth | D | 2-2 |
| Club Friendly List | 2018/07/19 18:00 | Weymouth v Exeter | L | 0-2 |
| Club Friendly List | 2018/07/14 14:00 | Weymouth v Kingstonian | W | 3-1 |
| England Southern League Premier | 2018/05/02 18:45 | Kings Lynn Town v Weymouth | L | 3-0 |
| England Southern League Premier | 2018/04/28 14:00 | Weymouth v Hitchin | W | 3-0 |
| England Southern League Premier | 2018/04/21 14:00 | Kings Langley v Weymouth | W | 2-3 |
| England Southern League Premier | 2018/04/19 18:45 | Kettering v Weymouth | L | 2-0 |