| Sat 12/08/23 | Market Drayton Town v Winsford United | 2-0 | | | | | | |
| Tue 15/08/23 | Winsford United v Stafford Town | 0-3 | | | | | | |
| Sat 19/08/23 | Winsford United v Stockport Town | 1-4 | | | | | | |
| 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 | | | | | | |
| Tue 05/09/23 | Winsford United v Droylsden | 1-3 | | | | | | |
| Sat 09/09/23 | Winsford United v Sandbach United * | 1-2 | | | | | | |
| Sat 16/09/23 | New Mills v Winsford United | 1-5 | | | | | |  |
| Sat 23/09/23 | Stafford Town v Winsford United | 2-7 | | | |  | | |
| Sat 30/09/23 | Winsford United v Abbey Hey | 2-3 | | | | | | |
| 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 | | | | | | |
| Sat 14/10/23 | Winsford United v Eccleshall | 2-0 | |  | | | | |
| Tue 17/10/23 | Winsford United v Chadderton (CUP) | 0-1 | | | | | | |
| Sat 28/10/23 | Winsford United v Stockport Georgians | 1-2 | | | | | | |
| Tue 31/10/23 | Stalybridge Celtic v Winsford United (CUP) * | 4-3 | | | | | | |
| Sat 04/11/23 | Droylsden v Winsford United | 2-1 | | | | | | |
| 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 27/01/24 | Maine Road v Winsford United | 1-3 | | | | | | |
| Sat 03/02/24 | Euxton Villa v Winsford United (CUP) | 1-1 | | | | | | |
| Wed 07/02/24 | Barnton v Winsford United (CUP) | 1-2 | | | | | | |
| Sat 10/02/24 | Witton Albion v Winsford United (CUP) * | 2-2 | | | | | | |
| Sat 02/03/24 | Stockport Town v Winsford United | 2-1 | | | | | | |
| Sat 09/03/24 | Eccleshall v Winsford United | 1-3 | | | | | | |
| Sat 16/03/24 | Winsford United v Market Drayton Town | 2-0 | | | | | | |
| Tue 19/03/24 | Winsford United v New Mills | 0-2 | | | | | | |
| Tue 26/03/24 | Winsford United v Cheadle Heath Nomads | 1-2 | | | | | | |
| Mon 01/04/24 | Barnton v Winsford United | 4-3 | | | | | | |
| 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 | | | | | | |
