| Date | Match |
|---|---|
| 07/08/19 | Eccleshall 0-5 FC Oswestry |
| 10/08/19 | FC Oswestry 5-1 Alsager Town 1 goal , MoM |
| 17/08/19 | Cheadle Town 1-5 FC Oswestry 2 goals , MoM |
| 20/08/19 | FC Oswestry 4-1 Cammell Laird |
| 24/08/19 | Sandbach 4-0 FC Oswestry |
| 26/08/19 | FC Oswestry 2-1 Vauxhall Mtrs 1 goal , MoM |
| 10/09/19 | New Mills 2-3 FC Oswestry 1 goal , Yellow Card , MoM |
| 21/09/19 | FC Oswestry 2-1 Wythenshawe Town |
| 23/09/19 | Maine Road 3-1 FC Oswestry |
| 27/09/19 | FC Oswestry 2-1 Barnton * |
| 26/10/19 | FC Oswestry 2-1 West Dids & Chor |
| 29/10/19 | FC Oswestry 2-1 St Martins 1 goal |
| 02/11/19 | Wythenshawe Am 0-1 FC Oswestry Yellow Card |
| 12/11/19 | Abbey Hey 1-1 FC Oswestry |
| 16/11/19 | FC Oswestry 1-3 Cheadle Town |
| 20/11/19 | Shawbury Utd 0-1 FC Oswestry |
| 25/11/19 | Stockport Town 3-2 FC Oswestry |
| 30/11/19 | FC Oswestry 1-1 Stone O.A. |
| 07/12/19 | Alsager Town 0-3 FC Oswestry |
* Indicates appearance as a substitute
| Competition | Teams Played For | Appearances |
|---|---|---|
| First Division South | FC Oswestry Town | 18 |
| TJ Vickers Premier Cup | FC Oswestry Town | 1 |
