| Date | Match |
|---|---|
| 06/08/19 | 1874 Northwich 3-1 Winsford United * |
| 10/08/19 | Vauxhall Mtrs 1-2 Winsford United |
| 17/08/19 | Winsford United 5-4 Squires Gate |
| 24/08/19 | Ramsbottom Utd 3-3 Winsford United |
| 26/08/19 | Congleton Town 4-3 Winsford United |
| 02/09/19 | Winsford United 1-3 Ramsbottom Utd |
* Indicates appearance as a substitute
| Competition | Teams Played For | Appearances |
|---|---|---|
| The Emirates F.A Cup | Winsford United | 3 |
| Premier Division | Winsford United | 3 |
