FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 |  | Worcester City | – | Dudley Town | | 3:0 (2:0) |
| Worcester |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Dudley Town | – | Market Drayton Town | | 0:6 |
| Dudley |
FA Cup 2013/14, Extra Preliminary Round |
| 21.08.2013 | | Dudley Town | – | Shawbury United | | 1:2 * |
| Dudley |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Dudley Town | – | Nuneaton Griff | | 0:1 |
| Dudley |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Bedworth United | – | Dudley Town | | 6:1 |
| |
FA Cup 2009/10, Preliminary Round |
| 01.09.2009 | | Bromsgrove Rovers | – | Dudley Town | | 3:0 * |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Dudley Town | – | Rainworth Miners Welfare | | 1:2 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 21.08.2007 | | Dudley Town | – | Glapwell | | 0:5 * |
| |
FA Cup 1996/97, Preliminary Round |
| | | Dudley Town | – | Tamworth | | 1:3 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Sandwell Borough | – | Dudley Town | | 2:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Dudley Town | – | Leek Town | | 0:1 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Raunds Town | – | Dudley Town | | 3:1 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Leicester United | – | Dudley Town | | 3:0 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Dudley Town | – | Lincoln United | | 1:4 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Corby Town | – | Dudley Town | | 1:0 * |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Dudley Town | – | Boston | | 0:1 |
| |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Grays Athletic | – | Dudley Town | | 2:0 * |
| |
FA Cup 1987/88, Preliminary Round |
| | | Rothwell Town | – | Dudley Town | | 2:1 * |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Stevenage Borough | – | Dudley Town | | 2:0 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Wisbech Town | – | Dudley Town | | 2:0 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Stalybridge Celtic | – | Dudley Town | | 3:1 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | March Town United | – | Dudley Town | | 3:2 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Dudley Town | – | Rushall Olympic | | 0:1 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Dudley Town | – | Malvern Town | | 0:2 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Moor Green | – | Dudley Town | | 2:1 * |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Sutton Coldfield Town | – | Dudley Town | | 4:1 |
| |
FA Cup 1978/79, Fourth Qualifying Round |
| | | Dudley Town | – | Worksop Town | | 0:1 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Dudley Town | – | AP Leamington | | 0:2 |
| |
FA Cup 1976/77, First Round Proper |
| 23.11.1976 | | York City | – | Dudley Town | | 4:1 * |
| York |
FA Cup 1975/76, Second Qualifying Round |
| | | Dudley Town | – | Nuneaton Borough | | 0:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Dudley Town | – | AP Leamington | | 1:3 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Dudley Town | – | Tamworth | | 1:2 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Moor Green | – | Dudley Town | | 2:1 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Dudley Town | – | Worcester City | | 0:1 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Dudley Town | – | Stourbridge | | 1:2 |
| |
FA Cup 1969/70, Third Qualifying Round |
| | | Tamworth | – | Dudley Town | | 2:0 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Dudley Town | – | Bilston | | 0:2 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Dudley Town | – | Burton Albion | | 0:4 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Stourbridge | – | Dudley Town | | 5:3 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Dudley Town | – | Worcester City | | 0:3 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Dudley Town | – | Worcester City | | 0:3 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Stafford Rangers | – | Dudley Town | | 11:0 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Lye Town | – | Dudley Town | | 6:0 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Kidderminster Harriers | – | Dudley Town | | 3:0 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Dudley Town | – | Hednesford Town | | 1:4 |
| |
FA Cup 1954/55, Preliminary Round |
| | | Stafford Rangers | – | Dudley Town | | 3:1 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Dudley Town | – | Bilston | | 1:2 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Kidderminster Harriers | – | Dudley Town | | 4:0 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Oswestry Town | – | Dudley Town | | 5:2 |
| |
FA Cup 1950/51, Second Qualifying Round |
| | | Dudley Town | – | Oswestry Town | | 0:1 |
| |
FA Cup 1949/50, Third Qualifying Round |
| | | Bromsgrove Rovers | – | Dudley Town | | 3:1 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Stourbridge | – | Dudley Town | | 3:1 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Stourbridge | – | Dudley Town | | 1:0 |
| |
FA Cup 1946/47, Second Qualifying Round |
| | | Nuneaton Borough | – | Dudley Town | | 2:1 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Bridgnorth Town | – | Dudley Town | | +:- |
| |
