| Sat 17/08/19 | Cheadle Town v FC Oswestry Town * | 1-5 | | | | | |
| Tue 20/08/19 | FC Oswestry Town v Cammell Laird 1907 * | 4-1 | | | | | |
| Sat 24/08/19 | Sandbach United v FC Oswestry Town | 4-0 | | | | | |
| Mon 26/08/19 | FC Oswestry Town v Vauxhall Motors | 2-1 | | | | | |
| Sat 07/09/19 | Steeton v FC Oswestry Town | 0-0 | | | | | |
| Tue 10/09/19 | New Mills v FC Oswestry Town | 2-3 | | | | | |
| Sat 14/09/19 | Gresley v FC Oswestry Town | 3-2 | | | | | |
| Sat 21/09/19 | FC Oswestry Town v Wythenshawe Town * | 2-1 | | | | | |
| Mon 23/09/19 | Maine Road v FC Oswestry Town | 3-1 | | |  | | |
| Fri 27/09/19 | FC Oswestry Town v Barnton | 2-1 | | | | | |
| Sat 05/10/19 | Garstang v FC Oswestry Town | - | | | | | |
| Sat 12/10/19 | Garstang v FC Oswestry Town | 2-2 | | | | | |
| Sat 19/10/19 | Maine Road v FC Oswestry Town | 3-0 | | | | | |
| Sat 26/10/19 | FC Oswestry Town v West Didsbury & Chorlton * | 2-1 | | | | | |
| Tue 29/10/19 | FC Oswestry Town v St Martins | 2-1 | | | | | |
| Sat 02/11/19 | Wythenshawe Amateurs v FC Oswestry Town | 0-1 | | | | | |
| Tue 12/11/19 | Abbey Hey v FC Oswestry Town | 1-1 | | | |  | |
| Sat 16/11/19 | FC Oswestry Town v Cheadle Town | 1-3 | | | | | |
| Sat 07/12/19 | Alsager Town v FC Oswestry Town | 0-3 |  | | | |  |
| Tue 10/12/19 | FC Oswestry Town v Cheadle Heath Nomads | 4-0 | | | | | |
| Sat 28/12/19 | Cheadle Heath Nomads v FC Oswestry Town | 2-4 | | | | | |
| Sat 04/01/20 | FC Oswestry Town v Wythenshawe Amateurs | 2-3 | | | | | |
| Tue 07/01/20 | FC Oswestry Town v Ellesmere Rangers | 3-3 | | | | | |
| Sat 11/01/20 | Wythenshawe Town v FC Oswestry Town | 1-2 | | | | | |
| Sat 18/01/20 | FC Oswestry Town v Abbey Hey | 2-1 | | | | | |
| Tue 21/01/20 | FC Oswestry Town v Wem Town | 8-0 | | | | | |
| Sat 01/02/20 | Stone Old Alleynians v FC Oswestry Town | 0-1 | | | | | |
| Tue 04/02/20 | FC Oswestry Town v Stockport Town | 0-1 | | | | | |
| Sat 08/02/20 | FC Oswestry Town v Emley AFC | 1-0 | | | | | |
