| Tue 03/08/21 | Winsford United v Macclesfield | 4-4 | | | | | |
| Sat 07/08/21 | Winsford United v Charnock Richard | 0-2 | | | | | |
| Sat 14/08/21 | Winsford United v Burscough | 3-1 | | | | | |
| Mon 30/08/21 | Winsford United v Irlam | 1-7 | | | | | |
| Sat 04/09/21 | Winsford United v Avro | 3-1 | | | | | |
| Sat 11/09/21 | Winsford United v Stapenhill | 3-1 | | | | | |
| Tue 14/09/21 | Winsford United v Northwich Victoria | 1-1 | | | | | |
| Sat 18/09/21 | Lower Breck v Winsford United | 4-3 | | | | | |
| Tue 21/09/21 | Vauxhall Motors v Winsford United | 4-1 | | | | | |
| Sat 25/09/21 | Winsford United v Gresley Rovers | 1-3 | | | | | |
| Sat 02/10/21 | Winsford United v Barnoldswick Town | 1-2 | | | | | |
| Tue 19/10/21 | Witton Albion v Winsford United | 1-3 | | | | | |
| Sat 23/10/21 | Runcorn Town v Winsford United | 0-3 | | | | |  |
| Tue 26/10/21 | Skelmersdale United v Winsford United | 2-2 | | | | | |
| Sat 30/10/21 | Congleton Town v Winsford United | 0-3 | | | | | |
| Sat 06/11/21 | Winsford United v Squires Gate | 6-2 | | | | | |
| Wed 10/11/21 | Litherland REMYCA v Winsford United | 2-2 | | | | | |
| Sat 13/11/21 | Winsford United v Longridge Town | 3-1 | | | | | |
| Sat 20/11/21 | Winsford United v Padiham | 1-1 | | | | | |
| Sat 27/11/21 | Irlam v Winsford United | 3-0 | | | | | |
| Tue 30/11/21 | Winsford United v Northwich Victoria | 3-0 | | | | | |
| Sat 18/12/21 | Barnoldswick Town v Winsford United | 2-2 | | | | | |
| Mon 27/12/21 | Macclesfield v Winsford United | 2-1 | | | | | |
| Mon 03/01/22 | Winsford United v Skelmersdale United | 3-2 | | |  | | |
| Wed 05/01/22 | Winsford United v Runcorn Linnets | 0-5 | | | | | |
