| Sat 09/09/23 | Barnton v Droylsden * | 1-0 | | | | | | |
| Tue 12/09/23 | Droylsden v Shelley (CUP) | 3-0 | |  | | | | |
| Sat 16/09/23 | Stockport Georgians v Droylsden | 3-1 |  | | | | |  |
| Sat 23/09/23 | Retford v Droylsden (CUP) | 1-1 | | | | | | |
| Sat 30/09/23 | Droylsden v Maine Road | 0-3 | | | | | | |
| Sat 07/10/23 | Droylsden v Sandbach United | 0-3 | | | | | | |
| Tue 10/10/23 | Ilkley Town v Droylsden (CUP) * | 3-4 | | | | | | |
| Sat 14/10/23 | Abbey Hey v Droylsden | 3-1 | | | | | | |
| Tue 24/10/23 | Stockport Georgians v Droylsden (CUP) | 3-0 | | | | | | |
| Sat 28/10/23 | Stockport Town v Droylsden | 1-1 | | | | | | |
| Sat 04/11/23 | Droylsden v Winsford United | 2-1 | | | | | | |
| Sat 11/11/23 | Droylsden v Nelson (CUP) | 5-1 | | | | | | |
| Tue 14/11/23 | Abbey Hey v Droylsden (CUP) | 1-5 | | | | | | |
| Sat 18/11/23 | Droylsden v Darwen FC (CUP) | 2-1 | | | | | | |
| Tue 21/11/23 | Droylsden v Stockport Georgians | 2-0 | | | | | | |
| Sat 25/11/23 | Droylsden v Stafford Town | 1-0 | | | | | | |
| Tue 05/12/23 | Curzon Ashton v Droylsden (CUP) | 7-2 | | | | | | |
| Sat 16/12/23 | Droylsden v Longridge Town (CUP) | 5-3 | | | | | | |
| Tue 19/12/23 | Droylsden v Ashville | 2-2 | | | | | | |
| Sat 23/12/23 | Eccleshall v Droylsden | 1-2 | | | | | | |
| Tue 26/12/23 | Droylsden v Market Drayton Town | 7-2 | | | | | | |
| Sat 06/01/24 | Droylsden v Stockport Town | 3-1 | | | | | | |
| Sat 13/01/24 | Abbey Hulton United v Droylsden | 3-1 | | | | | | |
| Sat 20/01/24 | Sandbach United v Droylsden | 4-3 | | | | | | |
| Sat 27/01/24 | Brocton v Droylsden | 1-2 | | | | | | |
| Sat 03/02/24 | Droylsden v Stockport Georgians (CUP) | 1-0 | | | | | | |
| Tue 13/02/24 | Droylsden v Barnton | 2-0 | | | | | | |
| Sat 17/02/24 | Droylsden v Ashville (CUP) | - | | | | | | |
| Sat 24/02/24 | New Mills v Droylsden | 3-3 | | | | | | |
| Sat 02/03/24 | Maine Road v Droylsden | 0-4 | | | | | | |
| Tue 05/03/24 | Droylsden v Ashville (CUP) | 1-0 | | | | | | |
| Sat 09/03/24 | Droylsden v Brocton | 0-1 | | | | | | |
| Sat 06/04/24 | Cheadle Heath Nomads v Droylsden * | 1-0 | | | | | | |
| Sat 13/04/24 | Droylsden v Eccleshall | 5-4 | | | | | | |
| Tue 16/04/24 | Chadderton v Droylsden (CUP) | 1-4 | | | | | | |
