Away History
| England FA Cup Qualification | 2018/10/20 14:00 | Torquay v Winchester City | L | 4-1 |
| England FA Cup Qualification | 2018/10/06 14:00 | Winchester City v Cirencester | W | 3-0 |
| England FA Cup Qualification | 2018/09/22 14:00 | Merthyr Town v Winchester City | W | 1-4 |
| England FA Cup Qualification | 2018/09/11 18:45 | Winchester City v Frome Town | W | 2-1 |
| England FA Cup Qualification | 2018/09/08 14:00 | Frome Town v Winchester City | D | 1-1 |
| Club Friendly List | 2018/08/04 14:00 | Winchester City v Weymouth | D | 2-2 |
| Club Friendly List | 2018/08/01 18:45 | Winchester City v Dorchester | W | 5-1 |
| Club Friendly List | 2018/07/28 14:00 | Winchester City v Eastleigh | W | 2-0 |