FA Cup 1985/86, First Qualifying Round |
 | | | GKN Sankey | – | Oswestry Town | | 1:0 * |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Frickley Athletic | – | Oswestry Town | | 2:0 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Congleton Town | – | Oswestry Town | | 3:0 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Horwich Railway Mechanics Institute | – | Oswestry Town | | 5:1 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Telford United | – | Oswestry Town | | 4:0 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Oswestry Town | – | Colwyn Bay | | 0:1 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Northwich Victoria | – | Oswestry Town | | 4:1 * |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Oswestry Town | – | Winsford United | | 0:1 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Oswestry Town | – | Rhyl | | 1:2 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Bethesda Athletic | – | Oswestry Town | | 2:1 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Northwich Victoria | – | Oswestry Town | | 3:1 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Oswestry Town | – | Doncaster Rovers | | 1:3 |
| |
FA Cup 1973/74, Preliminary Round |
| | | Oswestry Town | – | Northwich Victoria | | 1:3 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Marine | – | Oswestry Town | | 3:1 |
| |
FA Cup 1971/72, Fourth Qualifying Round |
| | | Oswestry Town | – | Altrincham | | 0:3 |
| |
FA Cup 1970/71, Third Qualifying Round |
| | | Rhyl | – | Oswestry Town | | 2:1 * |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Oswestry Town | – | Runcorn | | 0:1 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | South Liverpool | – | Oswestry Town | | 4:2 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Rhyl | – | Oswestry Town | | 4:0 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Oswestry Town | – | New Brighton | | 2:4 |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Oswestry Town | – | Kidderminster Harriers | | 3:4 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Macclesfield Town | – | Oswestry Town | | 2:0 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Bromsgrove Rovers | – | Oswestry Town | | 7:1 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Kidderminster Harriers | – | Oswestry Town | | 4:0 * |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Kidderminster Harriers | – | Oswestry Town | | 2:1 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Southend United | – | Oswestry Town | | 6:0 |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Oswestry Town | – | Kettering Town | | 1:3 |
| |
FA Cup 1957/58, First Round Proper |
| 16.11.1957 | | Oswestry Town | – | Bournemouth | | 1:5 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Oswestry Town | – | Stafford Rangers | | 0:4 * |
| |
FA Cup 1955/56, Preliminary Round |
| | | Stourbridge | – | Oswestry Town | | 6:0 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Oswestry Town | – | Bromsgrove Rovers | | 1:2 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Stourbridge | – | Oswestry Town | | 2:0 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Kidderminster Harriers | – | Oswestry Town | | 2:0 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Stourbridge | – | Oswestry Town | | 4:0 |
| |
FA Cup 1950/51, Third Qualifying Round |
| | | Oswestry Town | – | Hereford United | | 1:2 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Bilston | – | Oswestry Town | | 1:0 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Bromsgrove Rovers | – | Oswestry Town | | 5:0 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Oswestry Town | – | Bromsgrove Rovers | | 1:4 |
| |
FA Cup 1927/28, First Round Proper |
| 26.11.1927 | | Stockport County | – | Oswestry Town | | 5:2 |
| |
FA Cup 1887/88, Third Round |
| 26.11.1887 | | Stoke | – | Oswestry | | 3:0 |
| |
FA Cup 1887/88, First Round |
| 08.10.1887 | | Llangollen | – | Oswestry Town | | 7:3 * |
| |
FA Cup 1886/87, Second Round |
| 20.11.1886 | | Leek | – | Oswestry | | 4:2 |
| |
FA Cup 1884/85, First Round |
| 08.11.1884 | | Crewe Alexandra | – | Oswestry | | 2:1 |
| |
FA Cup 1883/84, Third Round |
| 29.12.1883 | | Oswestry Town | – | Queen's Park | | 1:7 |
| |
FA Cup 1882/83, First Round |
| 18.11.1882 | | Oswestry | – | Druids | | 0:2 * |
| |
FA Cup 1885/86, Second Round |
| | | Crewe Alexandra | – | Oswestry | | +:- * |
| |
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