| Sat 03/08/19 | Burscough v Winsford United | 1-3 | | | | | |
| Tue 06/08/19 | 1874 Northwich v Winsford United | 3-1 | | | | | |
| Sat 17/08/19 | Winsford United v Squires Gate | 5-4 | | | | | |
| Mon 19/08/19 | Winsford United v Hanley Town * | 1-2 | | | | | |
| Sat 24/08/19 | Ramsbottom United v Winsford United * | 3-3 |  | | | | |
| 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 21/09/19 | Charnock Richard v Winsford United | 4-1 | | | | | |
| 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 | | | | | |
| Tue 29/10/19 | Winsford United v Alsager Town | 2-1 | | | | | |
| Sat 02/11/19 | Winsford United v Burscough | 6-0 | | | | | |
| Sat 16/11/19 | Squires Gate v Winsford United | - | | | | | |
| Sat 23/11/19 | Winsford United v Charnock Richard * | 0-2 | | | | | |
| Wed 27/11/19 | Litherland REMYCA v Winsford United | 1-3 | | | | | |
| 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 | | | | | |
| Tue 17/12/19 | Squires Gate v Winsford United | 3-1 | | | | | |
| Sat 21/12/19 | Winsford United v Litherland REMYCA | 4-1 | | | | | |
| Sat 04/01/20 | Longridge Town v Winsford United | 5-3 | | | | | |
| 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 01/02/20 | Winsford United v Longridge Town | 0-0 | | | | | |
| Mon 03/02/20 | Winsford United v Whitchurch Alport | 1-2 | | | | | |
| Sat 08/02/20 | Runcorn Town v Winsford United | 2-2 | | | | | |
| Sun 08/03/20 | Winsford United v 1874 Northwich | 0-2 | | | | | |
| Wed 11/03/20 | Northwich Victoria v Winsford United | 1-1 | | | | | |
