| 26.11.20162016-11-26 16:00:00 | 16:00 | FA Trophy Qualification | 4. R | Winchester City - Dulwich Hamlet | 0:1 (0:1) |
| 12.11.20162016-11-12 16:00:00 | 16:00 | FA Trophy Qualification | 3. R | Phoenix Sports - Winchester City | 1:3 (1:2) |
| 29.10.20162016-10-29 16:00:00 | 16:00 | FA Trophy Qualification | 2. R | Fleet Town - Winchester City | 1:2 (1:1) |
| 11.10.20162016-10-11 20:45:00 | 20:45 | FA Trophy Qualification | 1. R | Petersfield Town - Winchester City | 1:3 |
| 8.10.20162016-10-8 16:00:00 | 16:00 | FA Trophy Qualification | 1. R | Winchester City - Petersfield Town | 1:1 |
| 1.10.20162016-10-1 16:00:00 | 16:00 | FA Cup Qualification | 3. R | Harrow Borough - Winchester City | 2:1 |
| 11.10.20162016-10-11 20:45:00 | 20:45 | FA Trophy Qualification | 1. R | Petersfield Town - Winchester City | 1:3 |
| 8.10.20162016-10-8 16:00:00 | 16:00 | FA Trophy Qualification | 1. R | Winchester City - Petersfield Town | 1:1 |
| 10.10.20152015-10-10 16:00:00 | 16:00 | FA Cup Qualification | 3. R | Petersfield Town - St.Albans | 0:1 |
| 3.10.20152015-10-3 16:00:00 | 16:00 | FA Trophy Qualification | 1. R | Petersfield Town - Winchester City | 1:3 |
| 26.9.20152015-9-26 16:00:00 | 16:00 | FA Cup Qualification | 2. R | Petersfield Town - Cirencester Town | 3:1 |
| 12.9.20152015-9-12 16:00:00 | 16:00 | FA Cup Qualification | 1. R | Petersfield Town - Weymouth | 3:1 |