| Date | Match |
|---|---|
| 03/08/19 | Burscough 1-3 Winsford United |
| 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 Yellow Card |
| 19/08/19 | Winsford United 1-2 Hanley Town |
| 26/08/19 | Congleton Town 4-3 Winsford United |
| 31/08/19 | Gresley 1-0 Winsford United |
| 07/09/19 | Winsford United 0-2 Rylands |
| 21/09/19 | Charnock Rich 4-1 Winsford United |
| 19/10/19 | Prestwich Heys 1-0 Winsford United |
| 22/10/19 | Bootle 1-0 Winsford United |
| 29/10/19 | Winsford United 2-1 Alsager Town |
| 02/11/19 | Winsford United 6-0 Burscough |
| 16/11/19 | Squires Gate - Winsford United |
| 23/11/19 | Winsford United 0-2 Charnock Rich |
| 27/11/19 | Lith REMYCA 1-3 Winsford United |
| 30/11/19 | Winsford United 0-5 Skelmersdale Utd |
| 03/12/19 | Barnoldswick Tn 2-1 Winsford United |
| 07/12/19 | Irlam 1-0 Winsford United |
| 17/12/19 | Squires Gate 3-1 Winsford United |
| 21/12/19 | Winsford United 4-1 Lith REMYCA |
* Indicates appearance as a substitute
| Competition | Teams Played For | Appearances |
|---|---|---|
| The Emirates F.A Cup | Winsford United | 1 |
| The Buildbase FA Vase | Winsford United | 1 |
| The Macron Cup | Winsford United | 1 |
| Premier Division | Winsford United | 17 |
| Cheshire Senior Cup | Winsford United | 1 |
