| Sat 29/07/23 | Alsager Town v Winsford United * | 5-0 | | | | | | |
| Tue 22/08/23 | Ashville v Winsford United * | 3-0 | | | | | | |
| Sat 26/08/23 | Armthorpe Welfare v Winsford United (CUP) * | 2-2 |  | | | | | |
| Mon 28/08/23 | Winsford United v Maine Road * | 0-1 | | | | | | |
| Sat 02/09/23 | Stockport Georgians v Winsford United * | 2-0 | | | | | | |
| Sat 09/09/23 | Winsford United v Sandbach United * | 1-2 | | | | | | |
| Sat 16/09/23 | New Mills v Winsford United * | 1-5 | | | | | | |
| Sat 07/10/23 | Winsford United v Abbey Hulton United * | 4-1 | | | | | | |
| Tue 10/10/23 | Abbey Hulton United v Winsford United (CUP) * | 1-5 | | | | | | |
| Tue 17/10/23 | Winsford United v Chadderton (CUP) * | 0-1 | | | | | | |
| Sat 28/10/23 | Winsford United v Stockport Georgians * | 1-2 | | | | | | |
| Sat 11/11/23 | Winsford United v Market Drayton Town (CUP) * | 6-0 | |  | | | | |
| Sat 16/12/23 | Abbey Hey v Winsford United * | 2-1 | | | | | | |
| Tue 26/12/23 | Winsford United v Barnton * | 0-4 | | | | | | |
| Sat 20/01/24 | Winsford United v Alsager Town * | 2-4 | | | | | | |
| Sat 27/01/24 | Maine Road v Winsford United * | 1-3 | | | | | | |
| Sat 02/03/24 | Stockport Town v Winsford United * | 2-1 | | | | | | |
| Sat 16/03/24 | Winsford United v Market Drayton Town * | 2-0 | | | | | | |
| Tue 19/03/24 | Winsford United v New Mills * | 0-2 | | | | | | |
| Sat 23/03/24 | Sandbach United v Winsford United * | 4-0 | | | | | | |
| Thu 04/04/24 | Winsford United v Ashville * | 4-0 | | | | | | |
| Mon 08/04/24 | Cheadle Heath Nomads v Winsford United * | 2-0 | | | | | | |
| Wed 10/04/24 | Winsford United v Cammell Laird 1907 * | 4-2 | | | | | | |
| Sat 13/04/24 | Brocton v Winsford United * | 3-0 | | | | | | |
