| Date Unknown | Cheshire Senior Cup 2nd Round | ||
|---|---|---|---|
| Winsford United | 0-2 | Northwich Victoria | |
| Saturday 7th September 1985 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Leek Town | 2-0 | Winsford United | Att: 211 |
| Saturday 5th October 1985 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| VS Rugby | 5-2 | Winsford United | Att: 389 |
| Saturday 16th November 1985 | League Challenge Cup 3rd Round | ||
|---|---|---|---|
| Winsford United | 1-1 | Fleetwood Town FC | |
| Wednesday 20th November 1985 | League Challenge Cup 3rd Round Replay | ||
|---|---|---|---|
| Fleetwood Town FC | 4-3 | Winsford United | |
| Saturday 25th January 1986 | Cheshire Senior Cup 1st Round | ||
|---|---|---|---|
| Winsford United | 1-1 | Cammell Laird | |
| Wednesday 5th February 1986 | Cheshire Senior Cup 1st Round Replay | ||
|---|---|---|---|
| Cammell Laird | 0-1 | Winsford United | |
| (played at Vauxhall) | |||
