| Date | Match |
|---|---|
| 23/08/19 | Barnton 1-0 Cheadle Town |
| 26/08/19 | Cheadle Town 0-7 Wythenshawe Town * |
| Date | Match |
|---|---|
| 07/09/19 | Winsford United 0-2 Rylands |
| 21/09/19 | Charnock Rich 4-1 Winsford United 1 goal |
| 05/10/19 | Skelmersdale Utd 0-1 Winsford United * |
| 07/10/19 | Winsford United 4-1 Padiham * |
| 12/10/19 | Winsford United 3-1 Avro |
| 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 1 goal |
| 16/11/19 | Squires Gate - Winsford United |
| 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 |
| 17/12/19 | Squires Gate 3-1 Winsford United |
* Indicates appearance as a substitute
| Competition | Teams Played For | Appearances |
|---|---|---|
| The Macron Cup | Winsford United | 1 |
| Premier Division | Winsford United | 12 |
| Cheshire Senior Cup | Winsford United | 1 |
| First Division South | Cheadle Town | 2 |
| Competition | Yellow Cards | Sin Bins | Red Cards |
|---|---|---|---|
| The Macron Cup | Winsford United | 1 | |
| Premier Division | Winsford United | 12 | |
| Cheshire Senior Cup | Winsford United | 1 | |
| First Division South | Cheadle Town | 2 |
