| Tue 06/08/19 | 1874 Northwich v Winsford United | 3-1 | | | | | |
| Sat 10/08/19 | Vauxhall Motors v Winsford United | 1-2 | | |  | | |
| Sat 17/08/19 | Winsford United v Squires Gate | 5-4 | | | | | |
| Mon 19/08/19 | Winsford United v Hanley Town | 1-2 | | | | | |
| Mon 26/08/19 | Congleton Town v Winsford United | 4-3 | | | | | |
| Sat 31/08/19 | Gresley v Winsford United | 1-0 | | | | | |
| Mon 02/09/19 | Winsford United v Ramsbottom United | 1-3 | | | | | |
| Sat 07/09/19 | Winsford United v Rylands | 0-2 | | | | | |
| Sat 28/09/19 | Winsford United v Ashton Athletic | 3-2 |  | | | | |
| Sat 05/10/19 | Skelmersdale United v Winsford United | 0-1 | | | | | |
| Mon 07/10/19 | Winsford United v Padiham | 4-1 | | | | | |
| Sat 12/10/19 | Winsford United v Avro | 3-1 | | | | | |
| Sat 19/10/19 | Prestwich Heys v Winsford United | 1-0 | | | | | |
| Tue 22/10/19 | Bootle v Winsford United | 1-0 | | | | | |
| Sat 16/11/19 | Squires Gate v Winsford United | - | | | | | |
| Sat 23/11/19 | Winsford United v Charnock Richard | 0-2 | | | | | |
| Sat 30/11/19 | Winsford United v Skelmersdale United | 0-5 | | | | | |
| Tue 03/12/19 | Barnoldswick Town v Winsford United | 2-1 | | | | | |
| Sat 07/12/19 | Irlam v Winsford United | 1-0 | | | | | |
| Sat 11/01/20 | Winsford United v Runcorn Town | 0-1 | | | | | |
| Sat 18/01/20 | Winsford United v Congleton Town | 2-2 | | | | | |
| Mon 20/01/20 | Winsford United v Hyde United | 2-4 | | | | | |
| Sat 25/01/20 | Avro v Winsford United | 2-2 | | | | | |
| Sat 08/02/20 | Runcorn Town v Winsford United | 2-2 | | | | | |
| Sun 08/03/20 | Winsford United v 1874 Northwich | 0-2 | | | | |  |
