| Sat 05/08/23 | Glossop North End v Colne (CUP) | 1-2 | | | | | | |
| Wed 16/08/23 | Glossop North End v FC Isle of Man | 0-4 | | | | | | |
| Sat 19/08/23 | Glossop North End v AFC Liverpool | 1-3 | | | | | | |
| Tue 22/08/23 | Padiham v Glossop North End | 0-1 | |  | | | | |
| Sat 26/08/23 | Glossop North End v Cheadle Heath Nomads (CUP) | 1-0 | | | | | | |
| 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 09/09/23 | Glossop North End v Pilkington | 2-0 | | | | | | |
| 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 07/10/23 | Pilkington v Glossop North End | 2-0 | | | | | | |
| Tue 10/10/23 | Glossop North End v Bury (CUP) | 2-1 | | | | | | |
| Sat 21/10/23 | FC Isle of Man v Glossop North End | 3-2 | | | | | | |
| Sat 23/12/23 | Charnock Richard v Glossop North End * | 2-2 | | | | | | |
| Tue 26/12/23 | Cheadle Town v Glossop North End | 0-1 | | | | | | |
| Sat 30/12/23 | Glossop North End v Litherland REMYCA | 3-3 | | | | | | |
| Sat 06/01/24 | Chadderton v Glossop North End | 1-4 | | | | | | |
| Sat 13/01/24 | Glossop North End v Wythenshawe | 0-1 | | | | | | |
| Thu 25/01/24 | Glossop North End v Ashville (CUP) | 2-3 | | | | | | |
| Sat 27/01/24 | Squires Gate v Glossop North End | 3-5 | | | | | | |
| Tue 30/01/24 | Prestwich Heys v Glossop North End | 3-2 | | |  | | | |
| Thu 01/02/24 | Trafford v Glossop North End (CUP) * | 1-1 | | | | | | |
| Sat 03/02/24 | Lower Breck v Glossop North End | 2-1 | | | | | | |
| Sat 10/02/24 | Glossop North End v Chadderton | 0-1 | | | | | | |
| Tue 13/02/24 | Glossop North End v Padiham | 4-3 | | | | | | |
| Sat 24/02/24 | Bury v Glossop North End | 1-0 | | | | | | |
| Sat 20/04/24 | Glossop North End v Charnock Richard * | 1-2 | | | | | | |
| Tue 23/04/24 | Colne v Glossop North End * | 1-1 | | | | | | |
