| Sat 29/07/23 | Cheadle Town v Charnock Richard | 0-1 | | | | | | |
| Tue 01/08/23 | Cheadle Town v Wythenshawe | 0-4 | | | |  | | |
| Sat 05/08/23 | Whitchurch Alport v Cheadle Town (CUP) | 2-1 | | | | | | |
| Wed 09/08/23 | Pilkington v Cheadle Town | 2-2 | | | | | | |
| Sat 12/08/23 | Skelmersdale United v Cheadle Town | 0-2 | |  | | | | |
| Tue 15/08/23 | Cheadle Town v Chadderton | 0-3 | | | | | | |
| Sat 19/08/23 | Cheadle Town v Litherland REMYCA | 4-1 | | | | | | |
| Tue 22/08/23 | Cheadle Town v Prestwich Heys | 2-4 | | | | | | |
| Sat 26/08/23 | Bury v Cheadle Town | 2-1 | | | | | | |
| Mon 28/08/23 | Cheadle Town v Colne | 1-2 | | | | | | |
| Sat 02/09/23 | Cheadle Town v Kendal Town | 1-3 | | | | | | |
| Tue 05/09/23 | Ramsbottom United v Cheadle Town | 2-0 | | | | | | |
| Sat 09/09/23 | Burscough v Cheadle Town | 1-4 | | | | | | |
| Thu 21/09/23 | Lower Breck v Cheadle Town | 0-0 | | | | | | |
| Sat 23/09/23 | Longridge Town v Cheadle Town | 1-1 | | | | | | |
| Tue 26/09/23 | Cheadle Town v Irlam | 2-5 |  | | | | | |
| Sat 30/09/23 | Cheadle Town v Skelmersdale United | 2-1 | | | | | | |
| Sat 07/10/23 | Cheadle Town v Longridge Town | 2-3 | | | | | | |
| Wed 11/10/23 | Northwich Victoria v Cheadle Town (CUP) | 1-3 | | | | | | |
| Sat 14/10/23 | AFC Liverpool v Cheadle Town | 1-3 | | | | | | |
| Tue 17/10/23 | Cheadle Town v Sandbach United (CUP) | 1-1 | | | | | | |
| Tue 24/10/23 | Cheadle Town v West Didsbury & Chorlton | 1-0 | | | | | | |
| Sat 28/10/23 | Ryton & Crawcrook Albion v Cheadle Town (CUP) | 3-5 | | | | | | |
| Sat 11/11/23 | Carlisle City v Cheadle Town (CUP) | 2-1 | | | | | | |
| Sat 18/11/23 | West Didsbury & Chorlton v Cheadle Town (CUP) | 0-3 | | | | | | |
| Tue 21/11/23 | Cheadle Town v Stockport Town (CUP) * | 1-1 | | | | | | |
| Sat 25/11/23 | FC Isle of Man v Cheadle Town | 0-1 | | | | | | |
| Tue 28/11/23 | Prestwich Heys v Cheadle Town | 2-1 | | | | | | |
