| 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 | | | | | | |
| 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 | | | | | | |
| Sat 09/09/23 | Burscough v Cheadle Town | 1-4 | | | | | | |
| Thu 21/09/23 | Lower Breck v Cheadle Town | 0-0 | |  | | | | |
| Tue 21/11/23 | Cheadle Town v Stockport Town (CUP) * | 1-1 | | | | | | |
| Sat 23/12/23 | Cheadle Town v Wythenshawe Town * | 0-4 | | | | | | |
| Tue 26/12/23 | Cheadle Town v Glossop North End | 0-1 | | | | | | |
| Sat 13/01/24 | Cheadle Town v AFC Liverpool * | 3-1 | | | | | | |
| Sat 27/01/24 | Wythenshawe Town v Cheadle Town * | 4-0 | | | | | | |
| Tue 30/01/24 | Cheadle Town v Warrington Town (CUP) * | 1-0 | | | | | | |
| Sat 03/02/24 | West Didsbury & Chorlton v Cheadle Town * | 2-0 | | | | | | |
| Sat 10/02/24 | Cheadle Town v Squires Gate | 2-4 | | | | | | |
| Tue 13/02/24 | Cheadle Town v Bury * | 0-2 | | | | | | |
| Sat 09/03/24 | Litherland REMYCA v Cheadle Town * | 4-4 | | | | | | |
| Sat 16/03/24 | Cheadle Town v FC Isle of Man | 3-2 | | | | | | |
| Tue 19/03/24 | Cheadle Town v Hyde United (CUP) * | 0-3 | | | | | | |
| Sat 06/04/24 | Cheadle Town v Ramsbottom United * | 0-1 | | | | | | |
| Thu 18/04/24 | Barnoldswick Town v Cheadle Town | 3-5 | | | | | | |
