FA Cup 2023/24, First Round Proper |
 | 04.11.2023 |  | Bristol Rovers | – | Whitby Town | | 7:2 (4:1) |
| Bristol |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Whitby Town | – | Marske United | | 0:1 (0:0) |
| Whitby |
FA Cup 2021/22, Third qualifying round |
| 02.10.2021 | | York City | – | Whitby Town | | 2:0 (2:0) |
| York |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Whitby Town | – | Warrington Rylands 1906 | | 1:2 |
| Whitby |
FA Cup 2019/20, Fourth Qualifying Round |
| 21.10.2019 | | Stourbridge | – | Whitby Town | | 3:2 (1:2) * |
| Stourbridge |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Whitley Bay | – | Whitby Town | | 1:0 (0:0) |
| Whitley Bay |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Penistone Church | – | Whitby Town | | 3:2 (2:2) |
| Penistone |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Spennymoor Town | – | Whitby Town | | 1:0 |
| Spennymoor |
FA Cup 2015/16, First Qualifying Round |
| 16.09.2015 | | Whitby Town | – | Salford City | | 0:5 (0:3) * |
| Whitby |
FA Cup 2014/15, First Qualifying Round |
| 17.09.2014 | | Whitby Town | – | Shildon | | 1:2 (1:1) * |
| Whitby |
FA Cup 2013/14, First Qualifying Round |
| 17.09.2013 | | West Auckland Town | – | Whitby Town | | 4:1 * |
| West Auckland |
FA Cup 2012/13, Third Qualifying Round |
| 06.10.2012 | | Stalybridge Celtic | – | Whitby Town | | 3:1 (2:1) |
| Stalybridge |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | Whitby Town | – | Blyth Spartans | | 1:2 (0:2) |
| |
FA Cup 2010/11, First Qualifying Round |
| 11.09.2010 | | Halifax Town | – | Whitby Town | | 2:0 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Whitby Town | – | Vauxhall Motors | | 0:5 |
| |
FA Cup 2008/09, Second Qualifying Round |
| 30.09.2008 | | Blyth Spartans | – | Whitby Town | | 5:2 * |
| |
FA Cup 2007/08, Second Qualifying Round |
| 29.09.2007 | | Bradford Park Avenue | – | Whitby Town | | 4:0 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Whitby Town | – | Frickley Athletic | | 2:4 |
| |
FA Cup 2005/06, Third Qualifying Round |
| 08.10.2005 | | Alfreton Town | – | Whitby Town | | 2:1 |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Whitby Town | – | Mossley | | 0:2 |
| |
FA Cup 2003/04, First Round Proper |
| 08.11.2003 | | Hartlepool United | – | Whitby Town | | 4:0 (2:0) |
| Hartlepool |
FA Cup 2002/03, Second Qualifying Round |
| | | Whitby Town | – | Bradford Park Avenue | | 0:4 |
| |
FA Cup 2001/02, First Round Proper |
| 27.11.2001 | | Plymouth Argyle | – | Whitby Town | | 3:2 (3:0) * |
| Plymouth |
FA Cup 2000/01, Third Qualifying Round |
| | | Easington Colliery | – | Whitby Town | | 1:0 |
| |
FA Cup 1997/98, Second Qualifying Round |
| | | Whitby Town | – | Winsford United | | 1:4 |
| |
FA Cup 1996/97, First Round Proper |
| 26.11.1996 | | Hull City | – | Whitby Town | | 8:4 (3:2) * |
| Kingston upon Hull |
FA Cup 1995/96, First Qualifying Round |
| | | Whitby Town | – | Billingham Town | | 0:1 |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Durham City | – | Whitby Town | | 3:1 * |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Whitby Town | – | Stalybridge Celtic | | 0:1 * |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Gateshead | – | Whitby Town | | 5:2 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Whitby Town | – | Garforth Town | | 0:1 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Whitby Town | – | Newcastle Blue Star | | 4:7 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Whitby Town | – | Hebburn | | 1:3 |
| |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Whitby Town | – | Barrow | | 1:3 * |
| |
FA Cup 1987/88, Fourth Qualifying Round |
| | | Macclesfield Town | – | Whitby Town | | 3:1 |
| |
FA Cup 1986/87, First Round Proper |
| 18.11.1986 | | Doncaster Rovers | – | Whitby Town | | 3:2 (2:1) * |
| Doncaster |
FA Cup 1985/86, Second Round Proper |
| 07.12.1985 | | York City | – | Whitby Town | | 3:1 |
| |
FA Cup 1984/85, First Round Proper |
| 17.11.1984 | | Whitby Town | – | Chesterfield | | 1:3 |
| |
FA Cup 1983/84, Second Round Proper |
| 10.12.1983 | | Wigan Athletic | – | Whitby Town | | 1:0 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Morecambe | – | Whitby Town | | 2:0 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Frickley Athletic | – | Whitby Town | | 2:0 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Whitby Town | – | Barrow | | 1:2 * |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Goole Town | – | Whitby Town | | 2:1 * |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Whitby Town | – | Yorkshire Amateur | | 1:2 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Boldon CA | – | Whitby Town | | 2:1 |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Whitby Town | – | Barrow | | 3:4 * |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Willington | – | Whitby Town | | 2:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Winterton Rangers | – | Whitby Town | | 3:2 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Wingate Durham | – | Whitby Town | | 2:1 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Whitby Town | – | Goole Town | | 0:1 |
| |
FA Cup 1971/72, Second Qualifying Round |
| | | Whitby Town | – | Scarborough | | 0:2 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | York City | – | Whitby Town | | 2:0 (1:0) |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Horden Colliery Welfare | – | Whitby Town | | 2:1 |
| |
FA Cup 1967/68, Third Qualifying Round |
| | | Whitby Town | – | Spennymoor United | | 0:1 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Billingham Synthonia | – | Whitby Town | | 1:0 * |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Crook Town | – | Whitby Town | | 4:1 * |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Stanley United | – | Whitby Town | | 2:0 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Bedlington Mechanics | – | Whitby Town | | 3:1 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Bedlington Mechanics | – | Whitby Town | | 4:2 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Whitby Town | – | Stockton | | 1:2 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Tow Law Town | – | Whitby Town | | 2:1 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Consett | – | Whitby Town | | 2:1 |
| |
FA Cup 1957/58, Second Qualifying Round |
| | | Willington | – | Whitby Town | | 5:2 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Whitby Town | – | Billingham Synthonia | | 2:3 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Whitby Town | – | Bridlington Central United | | 0:1 * |
| |
FA Cup 1954/55, First Qualifying Round |
| | | South Bank | – | Whitby Town | | 2:0 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Billingham Synthonia | – | Whitby Town | | 2:1 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Ferryhill Athletic | – | Whitby Town | | 4:0 |
| |
FA Cup 1951/52, Third Qualifying Round |
| | | Whitby Town | – | Billingham Synthonia | | 2:3 |
| |
FA Cup 1950/51, Third Qualifying Round |
| | | Scarborough | – | Whitby Town | | 3:0 |
| |
FA Cup 1945/46, Second Qualifying Round |
| | | Stockton | – | Whitby United | | 4:0 |
| |
