| 03/08/19 | Cheadle Heath 1-1 Stone O.A. |
| 10/08/19 | Cheadle Heath 3-0 Ellesmere Rngrs
Yellow Card |
| 17/08/19 | Barnton 0-2 Cheadle Heath |
| 24/08/19 | Maine Road 4-1 Cheadle Heath
Yellow Card |
| 26/08/19 | Cheadle Heath 1-2 Alsager Town |
| 31/08/19 | Cheadle Heath 5-3 Ashton Town |
| 07/09/19 | Cheadle Heath 1-4 Sandbach
Yellow Card |
| 21/09/19 | Cheadle Heath 1-1 Wythenshawe Am * |
| 24/09/19 | Abbey Hulton 1-3 Cheadle Heath
1 goal |
| 05/10/19 | Abbey Hulton 1-2 Cheadle Heath |
| 12/10/19 | Cheadle Heath 3-2 St Martins |
| 19/10/19 | Cheadle Heath 1-5 1874 Northwich
Yellow Card |
| 29/10/19 | Congleton Town 1-2 Cheadle Heath |
| 02/11/19 | West Dids & Chor 0-0 Cheadle Heath |
| 11/11/19 | Stockport Town 1-3 Cheadle Heath
1 goal |
| 16/11/19 | Cheadle Heath 1-0 Eccleshall |
| 19/11/19 | Cammell Laird 1-1 Cheadle Heath |
| 23/11/19 | Wythenshawe Town 4-1 Cheadle Heath
Yellow Card |
| 30/11/19 | Cheadle Heath 2-0 New Mills |
| 03/12/19 | Cheadle Heath 0-1 Cammell Laird |
| 07/12/19 | Stone O.A. 4-1 Cheadle Heath |
| 10/12/19 | FC Oswestry 4-0 Cheadle Heath
Yellow Card |
| 14/12/19 | Vauxhall Mtrs 2-1 Cheadle Heath |
| 26/12/19 | Cheadle Town 3-1 Cheadle Heath
Yellow Card |
| 28/12/19 | Cheadle Heath 2-4 FC Oswestry
Yellow Card |
| 04/01/20 | Eccleshall 2-0 Cheadle Heath |
| 07/01/20 | 1874 Northwich 3-0 Cheadle Heath
Yellow Card |
