| Tue 01/08/23 | Irlam v Glossop North End | 3-2 |  | | | | | |
| Sat 05/08/23 | Glossop North End v Colne (CUP) | 1-2 | | | | | | |
| Tue 08/08/23 | Glossop North End v Colne * | 1-2 | | | | | | |
| Sat 12/08/23 | Longridge Town v Glossop North End | 2-2 | | | | | | |
| Sat 19/08/23 | Glossop North End v AFC Liverpool | 1-3 | | | | | |  |
| Tue 22/08/23 | Padiham v Glossop North End * | 0-1 | |  | | | | |
| Tue 29/08/23 | Ramsbottom United v Glossop North End * | 2-3 | | | | | | |
| Sat 02/09/23 | Wythenshawe v Glossop North End * | 2-1 | | | | | | |
| Tue 05/09/23 | Glossop North End v Wythenshawe Town * | 2-2 | | | | | | |
| Sat 16/09/23 | Litherland REMYCA v Glossop North End | 1-0 | | | | | | |
| Tue 19/09/23 | Glossop North End v West Didsbury & Chorlton | 1-3 | | | | | | |
| Sat 23/09/23 | Irlam v Glossop North End (CUP) * | 4-4 | | | | | | |
| Tue 26/09/23 | Barnoldswick Town v Glossop North End | 3-2 | | | | | | |
| Sat 30/09/23 | Glossop North End v Bury | 2-1 | | | | | | |
| Tue 03/10/23 | Glossop North End v Ramsbottom United | 2-2 | | | | | | |
| Sat 21/10/23 | FC Isle of Man v Glossop North End | 3-2 | | | | | | |
| Sat 28/10/23 | Glossop North End v Irlam | 1-1 | | | | | | |
| Thu 02/11/23 | Lower Breck v Glossop North End (CUP) | 1-2 | | | | | | |
| Sat 04/11/23 | Skelmersdale United v Glossop North End | 0-1 | | | | | | |
| Sat 11/11/23 | Glossop North End v Lower Breck | 1-2 | | | | | | |
| Tue 14/11/23 | Glossop North End v New Mills (CUP) | 3-1 | | | | | | |
| Sat 25/11/23 | Wythenshawe Town v Glossop North End | 1-1 | | | | | | |
| Tue 12/12/23 | Glossop North End v Ashbourne (CUP) | 1-0 | | | | | | |
| Sat 16/12/23 | Glossop North End v Skelmersdale United | 0-1 | | | | | | |
| Tue 19/12/23 | Glossop North End v Longridge Town | 2-1 | | | | | | |
| Sat 23/12/23 | Charnock Richard v Glossop North End | 2-2 | | | | | | |
| Tue 26/12/23 | Cheadle Town v Glossop North End | 0-1 | | | | | | |
| Thu 25/01/24 | Glossop North End v Ashville (CUP) | 2-3 | | | | | | |
| Sat 24/02/24 | Bury v Glossop North End * | 1-0 | | | | | | |
| Tue 27/02/24 | Glossop North End v Kendal Town | 0-1 | | | | | | |
| Sat 09/03/24 | Glossop North End v Prestwich Heys | 0-1 | | | | | | |
| Sat 16/03/24 | West Didsbury & Chorlton v Glossop North End | 1-2 | | | | | | |
| Mon 01/04/24 | Glossop North End v Cheadle Town | 1-2 | | | | | | |
| Sat 06/04/24 | Burscough v Glossop North End | 2-2 | | | | | | |
| Sat 13/04/24 | AFC Liverpool v Glossop North End | 3-2 | | | | | | |
| Sat 20/04/24 | Glossop North End v Charnock Richard | 1-2 | | | | | | |
| Tue 23/04/24 | Colne v Glossop North End | 1-1 | | | | | | |
