| Mon 05/08/19 | Stockport Town v Cheadle Town | 2-2 | | |  | | |
| Sat 10/08/19 | Cheadle Town v St Martins | 0-1 | | | | | |
| Sat 17/08/19 | Cheadle Town v FC Oswestry Town | 1-5 | | | | | |
| Tue 20/08/19 | West Didsbury & Chorlton v Cheadle Town | 2-1 | | | | | |
| Fri 23/08/19 | Barnton v Cheadle Town | 1-0 | | | | | |
| Mon 26/08/19 | Cheadle Town v Wythenshawe Town | 0-7 | | | | | |
| Sat 31/08/19 | Staveley Miners Welfare v Cheadle Town | 2-5 |  | | | | |
| Sat 07/09/19 | Cleator Moor Celtic v Cheadle Town | 1-2 | | | | | |
| Tue 10/09/19 | Wythenshawe Amateurs v Cheadle Town | 0-1 | | | | | |
| Sat 14/09/19 | Cheadle Town v East Hull FC | 4-0 | | | | | |
| Sat 21/09/19 | Vauxhall Motors v Cheadle Town | 4-2 | | | | | |
| Sat 28/09/19 | Cheadle Town v Abbey Hulton United | 4-1 | | | | | |
| Sat 05/10/19 | Alsager Town v Cheadle Town | 2-5 | | | | | |
| Wed 09/10/19 | Cheadle Town v Eccleshall | 2-2 | | | | | |
| Sat 12/10/19 | Selby Town v Cheadle Town | 5-1 | | | | | |
| Wed 16/10/19 | Stone Old Alleynians v Cheadle Town | 1-1 | | | | | |
| Sat 16/11/19 | FC Oswestry Town v Cheadle Town | 1-3 | | | | | |
| Tue 19/11/19 | Wythenshawe Amateurs v Cheadle Town * | 3-2 | | | | | |
| Sat 23/11/19 | Cheadle Town v Wythenshawe Amateurs | 4-2 | | | | | |
| Wed 27/11/19 | Cheadle Town v Abbey Hey | 0-1 | | | | | |
| Sat 14/12/19 | St Martins v Cheadle Town | 1-6 | | | | | |
| Wed 18/12/19 | Cheadle Town v Stone Old Alleynians | 1-2 | | | | | |
| Sat 21/12/19 | Cheadle Town v Alsager Town | 1-2 | | | | | |
| Thu 26/12/19 | Cheadle Town v Cheadle Heath Nomads | 3-1 | | | | | |
| Sat 28/12/19 | Eccleshall v Cheadle Town | 0-4 | | | | | |
| Sat 04/01/20 | Cheadle Town v Sandbach United | 1-0 | | | |  | |
| Sat 25/01/20 | Cheadle Town v Stockport Town | 2-1 | | | | | |
| Mon 27/01/20 | Maine Road v Cheadle Town | 2-2 | | | | | |
| Sat 01/02/20 | Wythenshawe Town v Cheadle Town | 2-0 | | | | | |
| Sat 08/02/20 | AFC Liverpool v Cheadle Town | 3-0 | | | | | |
| Wed 12/02/20 | Cheadle Town v Vauxhall Motors | 0-1 | | | | | |
| Sat 07/03/20 | Cheadle Town v Maine Road | 2-1 | | | | | |
| Sat 14/03/20 | Cheadle Town v New Mills | 1-1 | | | | | |
