| Date | Match |
|---|---|
| 03/08/19 | Burscough 1-3 Winsford United |
| 06/08/19 | 1874 Northwich 3-1 Winsford United |
| 17/08/19 | Winsford United 5-4 Squires Gate |
| 19/08/19 | Winsford United 1-2 Hanley Town * |
| 24/08/19 | Ramsbottom Utd 3-3 Winsford United * 1 goal |
| 26/08/19 | Congleton Town 4-3 Winsford United |
| 31/08/19 | Gresley 1-0 Winsford United |
| 02/09/19 | Winsford United 1-3 Ramsbottom Utd Yellow Card |
| 07/09/19 | Winsford United 0-2 Rylands * |
| 21/09/19 | Charnock Rich 4-1 Winsford United Yellow Card |
* Indicates appearance as a substitute
| Competition | Teams Played For | Appearances |
|---|---|---|
| The Emirates F.A Cup | Winsford United | 2 |
| The Buildbase FA Vase | Winsford United | 1 |
| Premier Division | Winsford United | 7 |
