| Sat 03/08/19 | Eccleshall v West Didsbury & Chorlton | 0-4 | | | | |
| Tue 06/08/19 | West Didsbury & Chorlton v Wythenshawe Town | 1-1 | | | | |
| Sat 10/08/19 | Squires Gate v West Didsbury & Chorlton | 1-2 |  | | | |
| Tue 13/08/19 | West Didsbury & Chorlton v Stockport Town | 1-0 | | | |  |
| Sat 24/08/19 | Stalybridge Celtic v West Didsbury & Chorlton * | 0-0 | | | | |
| Mon 26/08/19 | Barnton v West Didsbury & Chorlton | 0-1 | | | | |
| Tue 03/09/19 | West Didsbury & Chorlton v Stalybridge Celtic | 2-3 | | | | |
| Tue 10/09/19 | West Didsbury & Chorlton v Abbey Hulton United | 5-0 | | | | |
| Sat 14/09/19 | Runcorn Town v West Didsbury & Chorlton | 0-1 | | | | |
| Sat 21/09/19 | West Didsbury & Chorlton v Stone Old Alleynians | 0-2 | | | | |
| Tue 24/09/19 | New Mills v West Didsbury & Chorlton | 3-3 | | | | |
| Sat 28/09/19 | Cammell Laird 1907 v West Didsbury & Chorlton | 1-2 | |  | | |
| Sat 05/10/19 | West Didsbury & Chorlton v Nelson | 4-0 | | | | |
| Tue 08/10/19 | West Didsbury & Chorlton v Trafford * | 1-2 | | | | |
| Sat 12/10/19 | Shildon v West Didsbury & Chorlton | 2-0 | | | | |
| Sat 19/10/19 | West Didsbury & Chorlton v New Mills | 3-1 | | | | |
| Sat 26/10/19 | FC Oswestry Town v West Didsbury & Chorlton | 2-1 | | | | |
| Sat 02/11/19 | West Didsbury & Chorlton v Cheadle Heath Nomads | 0-0 | | | | |
| Sat 09/11/19 | West Didsbury & Chorlton v Alsager Town | 6-1 | | | | |
| Sat 16/11/19 | Wythenshawe Town v West Didsbury & Chorlton | - | | | | |
| Sat 23/11/19 | St Helens Town v West Didsbury & Chorlton | 1-2 | | | | |
| Tue 26/11/19 | West Didsbury & Chorlton v Alsager Town | 4-1 | | | | |
| Sat 30/11/19 | Ellesmere Rangers v West Didsbury & Chorlton | 3-2 | | | | |
| Tue 03/12/19 | Vauxhall Motors v West Didsbury & Chorlton | 3-0 | | | | |
