FA Cup 2023/24, Fourth Qualifying Round |
 | 17.10.2023 | | Whitby Town | – | Chelmsford City | | 3:1 (2:0) * |
| Whitby |
FA Cup 2023/24, Third Qualifying Round |
| 30.09.2023 | | Whitby Town | – | Morpeth Town | | 1:0 (0:0) |
| Whitby |
FA Cup 2023/24, Second Qualifying Round |
| 16.09.2023 | | Whitby Town | – | Prescot Cables | | 2:1 (2:1) |
| Whitby |
FA Cup 2023/24, First Qualifying Round |
| 01.09.2023 | | Goole AFC | – | Whitby Town | | 0:6 (0:2) |
| Goole |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Whitby Town | – | Bishop Auckland | | 5:0 (2:0) |
| Whitby |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Prescot Cables | – | Whitby Town | | 0:3 (0:1) |
| Prescot |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Warrington Rylands 1906 | – | Whitby Town | | 0:4 (0:0) |
| Warrington |
FA Cup 2019/20, Third Qualifying Round |
| 07.10.2019 | | Gloucester City | – | Whitby Town | | 1:3 (0:1) * |
| Cheltenham |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | 1874 Northwich | – | Whitby Town | | 0:1 (0:1) |
| Winsford |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Widnes | – | Whitby Town | | 0:4 (0:1) |
| Widnes |
FA Cup 2016/17, First Qualifying Round |
| 05.09.2016 | | Winsford United | – | Whitby Town | | 1:2 * |
| Winsford |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Whitby Town | – | Droylsden | | 4:3 (1:0) |
| Whitby |
FA Cup 2012/13, First Qualifying Round |
| 12.09.2012 | | Whitby Town | – | Ossett Town | | 1:0 (0:0) * |
| Whitby |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Whitby Town | – | North Ferriby United | | 2:1 (0:1) |
| |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Parkgate | – | Whitby Town | | 1:3 |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Bridlington Town | – | Whitby Town | | 0:1 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Whitby Town | – | Dunston Federation | | 3:2 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Whitby Town | – | Shildon | | 3:2 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 28.09.2005 | | Whitby Town | – | Trafford | | 6:0 * |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Newcastle Blue Star | – | Whitby Town | | 1:2 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Billingham Synthonia | – | Whitby Town | | 1:3 |
| |
FA Cup 2003/04, Fourth Qualifying Round |
| | | Whitby Town | – | Bromsgrove Rovers | | 2:1 (1:1) * |
| |
FA Cup 2003/04, Third Qualifying Round |
| | | Whitby Town | – | Warrington Town | | 2:1 * |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Whitby Town | – | Winsford United | | 3:0 |
| |
FA Cup 2001/02, Fourth Qualifying Round |
| | | Whitby Town | – | Scarborough | | 3:1 (1:1) |
| |
FA Cup 2001/02, Third Qualifying Round |
| | | Whitby Town | – | Spennymoor United | | 3:0 (1:0) |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Whitby Town | – | Ramsbottom United | | 5:2 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Chorley | – | Whitby Town | | 0:2 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Accrington Stanley | – | Whitby Town | | 0:2 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Whitby Town | – | Accrington Stanley | | 4:2 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Whitby Town | – | Netherfield | | 6:2 |
| |
FA Cup 1996/97, Fourth Qualifying Round |
| | | Whitby Town | – | Blyth Spartans | | 2:1 |
| |
FA Cup 1996/97, Third Qualifying Round |
| | | Farsley Celtic | – | Whitby Town | | 0:1 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Hyde United | – | Whitby Town | | 0:1 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Garforth Town | – | Whitby Town | | 1:3 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Whitby Town | – | Whickham | | 6:2 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Whitby Town | – | Willington | | 6:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | West Auckland Town | – | Whitby Town | | 0:2 |
| |
FA Cup 1993/94, Third Qualifying Round |
| | | Lancaster City | – | Whitby Town | | 1:2 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Spennymoor United | – | Whitby Town | | 2:3 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Whitby Town | – | Crook Town | | 5:1 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Shildon | – | Whitby Town | | 0:2 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Willington | – | Whitby Town | | 1:5 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Whitby Town | – | Leyland DAF | | 2:0 |
| |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Whitby Town | – | Newcastle Blue Star | | 2:0 |
| |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Whitby Town | – | South Liverpool | | 1:0 |
| |
FA Cup 1985/86, Fourth Qualifying Round |
| | | Peterlee Newtown | – | Whitby Town | | 0:1 * |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Marine | – | Whitby Town | | 0:1 |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Whitby Town | – | Ryhope CA | | 5:1 * |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Whitby Town | – | North Shields | | 2:0 * |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Willington | – | Whitby Town | | 2:5 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Halifax Town | – | Whitby Town | | 2:3 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Whitby Town | – | Bishop Auckland | | 4:2 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Whitby Town | – | Lancaster City | | 7:3 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Durham City | – | Whitby Town | | 1:3 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Harrogate Town | – | Whitby Town | | 2:4 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Whitby Town | – | South Bank | | 3:0 |
| |
FA Cup 1980/81, Preliminary Round |
| | | Whitby Town | – | Yorkshire Amateur | | 3:1 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Whitby Town | – | Frickley Athletic | | 3:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Whitby Town | – | Thackley | | 2:0 * |
| |
FA Cup 1979/80, Preliminary Round |
| | | Normanby Park Steel Works | – | Whitby Town | | 1:3 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Worsbrough Bridge Miners Welfare | – | Whitby Town | | 0:1 * |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Tow Law Town | – | Whitby Town | | 0:4 |
| |
FA Cup 1977/78, Preliminary Round |
| | | Wallsend Town | – | Whitby Town | | 2:3 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Whitby Town | – | Whitley Bay | | 2:0 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Whitby Town | – | Spennymoor United | | 3:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Whitby Town | – | Wingate Durham | | 4:0 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Bridlington Trinity | – | Whitby Town | | 0:1 * |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Hull Brunswick | – | Whitby Town | | 1:3 |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Whitby Town | – | Scarborough | | 3:1 |
| |
FA Cup 1969/70, Third Qualifying Round |
| | | Evenwood Town | – | Whitby Town | | 0:2 |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | Whitby Town | – | Wingate Durham | | 3:1 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Bedlington Colliery Welfare | – | Whitby Town | | 0:1 |
| |
FA Cup 1969/70, Preliminary Round |
| | | Whitby Town | – | West Auckland Town | | 3:1 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Whitby Town | – | Blyth Spartans | | 2:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Billingham Synthonia | – | Whitby Town | | 2:6 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Consett | – | Whitby Town | | 2:3 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Whitby Town | – | Spennymoor United | | 4:3 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Willington | – | Whitby Town | | 1:2 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Billingham Synthonia | – | Whitby Town | | 1:2 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Spennymoor United | – | Whitby Town | | 0:2 * |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Whitby Town | – | Willington | | 4:2 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Whitby Town | – | Tow Law Town | | 5:1 * |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Whitby Town | – | South Bank | | 5:1 |
| |
FA Cup 1951/52, Second Qualifying Round |
| | | Whitby Town | – | South Bank | | 3:2 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Whitby Town | – | Bridlington Central United | | 6:2 |
| |
FA Cup 1950/51, Second Qualifying Round |
| | | Whitby Town | – | Head Wrightsons | | 4:2 |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Whitby Town | – | Cargo Fleet Works | | 10:2 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Skinnigrove Works | – | Whitby Town | | 0:5 |
| |
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