FA Cup 2023/24, Fourth Qualifying Round |
 | 14.10.2023 |  | Chelmsford City | – | Whitby Town | | 2:2 (0:1) |
| Chelmsford |
FA Cup 2019/20, Fourth Qualifying Round |
| 19.10.2019 | | Whitby Town | – | Stourbridge | | 1:1 (0:0) |
| Whitby |
FA Cup 2019/20, Third Qualifying Round |
| 05.10.2019 | | Whitby Town | – | Gloucester City | | 1:1 (0:0) |
| Whitby |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Whitby Town | – | Winsford United | | 3:3 |
| Whitby |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Salford City | – | Whitby Town | | 1:1 (0:1) |
| Salford |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Shildon | – | Whitby Town | | 1:1 (1:1) |
| Shildon |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Whitby Town | – | West Auckland Town | | 1:1 |
| Whitby |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Ossett Town | – | Whitby Town | | 1:1 (0:1) |
| Ossett |
FA Cup 2008/09, Second Qualifying Round |
| 27.09.2008 | | Whitby Town | – | Blyth Spartans | | 2:2 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Trafford | – | Whitby Town | | 1:1 |
| |
FA Cup 2003/04, Fourth Qualifying Round |
| | | Bromsgrove Rovers | – | Whitby Town | | 2:2 (1:1) |
| |
FA Cup 2003/04, Third Qualifying Round |
| | | Warrington Town | – | Whitby Town | | 0:0 |
| |
FA Cup 2001/02, First Round Proper |
| 17.11.2001 | | Whitby Town | – | Plymouth Argyle | | 1:1 (1:0) |
| Whitby |
FA Cup 1999/00, Third Qualifying Round |
| | | Whitby Town | – | Lancaster City | | 2:2,
pen. 2:4 * |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Lancaster City | – | Whitby Town | | 2:2 |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Bedlington Terriers | – | Whitby Town | | 1:1,
pen. 4:3 * |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Whitby Town | – | Bedlington Terriers | | 1:1 |
| |
FA Cup 1996/97, First Round Proper |
| 17.11.1996 | | Whitby Town | – | Hull City | | 0:0 |
| Whitby |
FA Cup 1994/95, Third Qualifying Round |
| | | Whitby Town | – | Durham City | | 1:1 |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Stalybridge Celtic | – | Whitby Town | | 0:0 |
| |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Barrow | – | Whitby Town | | 1:1 |
| |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Whitby Town | – | Doncaster Rovers | | 2:2 (0:1) |
| Whitby |
FA Cup 1985/86, Fourth Qualifying Round |
| | | Whitby Town | – | Peterlee Newtown | | 2:2 |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Ryhope CA | – | Whitby Town | | 1:1 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | North Shields | – | Whitby Town | | 2:2 aet * |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Whitby Town | – | North Shields | | 1:1 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Lancaster City | – | Whitby Town | | 2:2 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Barrow | – | Whitby Town | | 1:1 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Whitby Town | – | Goole Town | | 2:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Thackley | – | Whitby Town | | 2:2 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Whitby Town | – | Worsbrough Bridge Miners Welfare | | 3:3 |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Barrow | – | Whitby Town | | 2:2 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Whitby Town | – | Bridlington Trinity | | 1:1 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Whitby Town | – | Billingham Synthonia | | 1:1 |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Whitby Town | – | Crook Town | | 1:1 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Whitby Town | – | Spennymoor United | | 2:2 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Tow Law Town | – | Whitby Town | | 2:2 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Bridlington Central United | – | Whitby Town | | 4:4 |
| |
