FA Cup 2007/08, First Qualifying Round |
 | 15.09.2007 |  | Bradford Park Avenue | – | Scarborough | | +:- |
| |
FA Cup 2006/07, Fourth Qualifying Round |
| 28.10.2006 | | Stafford Rangers | – | Scarborough | | 3:0 (2:0) |
| |
FA Cup 2005/06, Fourth Qualifying Round |
| 22.10.2005 | | Harrogate Town | – | Scarborough | | 1:0 (0:0) |
| |
FA Cup 2004/05, Fourth Qualifying Round |
| | | Scarborough | – | Lancaster City | | 0:1 (0:0) * |
| |
FA Cup 2003/04, Fourth Round Proper |
| 24.01.2004 | | Scarborough | – | Chelsea | | 0:1 (0:1) |
| Scarborough |
FA Cup 2002/03, First Round Proper |
| 26.11.2002 | | Cambridge United | – | Scarborough | | 2:1 aet
(1:0, 1:1) * |
| Cambridge |
FA Cup 2001/02, Fourth Qualifying Round |
| | | Whitby Town | – | Scarborough | | 3:1 (1:1) |
| |
FA Cup 2000/01, Fourth Qualifying Round |
| | | Scarborough | – | Leigh Railway Mechanics Institute | | 3:4 (0:3) |
| Scarborough |
FA Cup 1999/00, Fourth Qualifying Round |
| | | Scarborough | – | Tamworth | | 0:1 (0:1) |
| |
FA Cup 1998/99, First Round Proper |
| 24.11.1998 | | Rochdale | – | Scarborough | | 2:0 (1:0) * |
| Rochdale |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Scunthorpe United | – | Scarborough | | 2:1 (1:0) |
| Scunthorpe |
FA Cup 1996/97, Second Round Proper |
| 07.12.1996 | | Chesterfield | – | Scarborough | | 2:0 (1:0) |
| Chesterfield |
FA Cup 1995/96, First Round Proper |
| 11.11.1995 | | Scarborough | – | Chesterfield | | 0:2 (0:0) |
| Scarborough |
FA Cup 1994/95, Third Round Proper |
| 17.01.1995 | | Watford | – | Scarborough | | 2:0 (0:0) * |
| Watford |
FA Cup 1993/94, Second Round Proper |
| 04.12.1993 | | Wigan Athletic | – | Scarborough | | 1:0 (0:0) |
| Wigan |
FA Cup 1992/93, First Round Proper |
| 14.11.1992 | | Burnley | – | Scarborough | | 2:1 (1:0) |
| Burnley |
FA Cup 1991/92, First Round Proper |
| 16.11.1991 | | Scarborough | – | Wigan Athletic | | 0:2 |
| Scarborough |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Scarborough | – | Leek Town | | 0:2 |
| Scarborough |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Scarborough | – | Whitley Bay | | 0:1 |
| Scarborough |
FA Cup 1988/89, Second Round Proper |
| 10.12.1988 | | Scarborough | – | Carlisle United | | 0:1 (0:0) |
| Scarborough |
FA Cup 1987/88, First Round Proper |
| 14.11.1987 | | Scarborough | – | Grimsby Town | | 1:2 (0:1) |
| Scarborough |
FA Cup 1986/87, First Qualifying Round |
| | | Goole Town | – | Scarborough | | 2:1 |
| |
FA Cup 1985/86, First Round Proper |
| 17.11.1985 | | Notts County | – | Scarborough | | 6:1 |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Tow Law Town | – | Scarborough | | 1:0 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| |  | Bangor City | – | Scarborough | | 2:1 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Tranmere Rovers | – | Scarborough | | 4:2 |
| |
FA Cup 1981/82, Fourth Qualifying Round |
| | | Scarborough | – | Blyth Spartans | | 2:3 |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Burnley | – | Scarborough | | 1:0 |
| |
FA Cup 1979/80, First Round Proper |
| 24.11.1979 | | Halifax Town | – | Scarborough | | 2:0 |
| |
FA Cup 1978/79, Second Round Proper |
| 16.12.1978 | | York City | – | Scarborough | | 3:0 |
| |
FA Cup 1977/78, Third Round Proper |
| 07.01.1978 | | Brighton & Hove Albion | – | Scarborough | | 3:0 |
| |
FA Cup 1976/77, First Round Proper |
| 22.11.1976 | | Darlington | – | Scarborough | | 4:1 * |
| Darlington |
FA Cup 1975/76, Third Round Proper |
| 03.01.1976 | | Scarborough | – | Crystal Palace | | 1:2 |
| |
FA Cup 1974/75, Fourth Qualifying Round |
| | | Blyth Spartans | – | Scarborough | | 3:1 |
| |
FA Cup 1973/74, Second Round Proper |
| 15.12.1973 | | Port Vale | – | Scarborough | | 2:1 |
| |
FA Cup 1972/73, Second Round Proper |
| 09.12.1972 | | Scarborough | – | Doncaster Rovers | | 1:2 |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Hartlepool | – | Scarborough | | 6:1 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Scarborough | – | Workington | | 2:3 |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Whitby Town | – | Scarborough | | 3:1 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Scarborough | – | Goole Town | | 0:2 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Goole Town | – | Scarborough | | 2:1 * |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Scarborough | – | Bridlington Trinity | | 1:2 |
| |
FA Cup 1965/66, First Round Proper |
| 13.11.1965 | | Altrincham | – | Scarborough | | 6:0 |
| |
FA Cup 1964/65, Second Round Proper |
| 09.12.1964 | | Scarborough | – | Doncaster Rovers | | 1:2 * |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Scarborough | – | Tow Law Town | | 0:2 |
| |
FA Cup 1962/63, First Round Proper |
| 07.11.1962 | | Scarborough | – | Crewe Alexandra | | 2:3 * |
| |
FA Cup 1961/62, Fourth Qualifying Round |
| | | Ashington | – | Scarborough | | 2:0 * |
| |
FA Cup 1960/61, First Round Proper |
| 09.11.1960 | | Scarborough | – | Bradford City | | 1:2 * |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Bradford Park Avenue | – | Scarborough | | 6:1 |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Scarborough | – | Heanor Town | | 2:3 * |
| |
FA Cup 1957/58, First Round Proper |
| 16.11.1957 | | Bradford City | – | Scarborough | | 6:0 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Rhyl | – | Scarborough | | 3:2 |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Workington | – | Scarborough | | 4:2 |
| |
FA Cup 1954/55, First Round Proper |
| 20.11.1954 | | York City | – | Scarborough | | 3:2 |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Wigan Athletic | – | Scarborough | | 4:0 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Scarborough | – | Mansfield Town | | 0:8 |
| |
FA Cup 1951/52, Fourth Qualifying Round |
| | | Blackhall Colliery Welfare | – | Scarborough | | 5:3 * |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Scarborough | – | Rhyl | | 1:2 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Scarborough | – | North Shields | | 1:3 * |
| |
FA Cup 1948/49, Second Round Proper |
| 11.12.1948 | | Gateshead | – | Scarborough | | 3:0 |
| |
FA Cup 1947/48, Fourth Qualifying Round |
| | | Scarborough | – | South Shields | | 2:3 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Stockton | – | Scarborough | | 5:1 |
| |
FA Cup 1945/46, Fourth Qualifying Round |
| | | Scarborough | – | North Shields | | 2:4 |
| |
FA Cup 1938/39, First Round Proper |
| 29.11.1938 | | Southport | – | Scarborough | | 5:3 * |
| |
FA Cup 1937/38, Third Round Proper |
| 12.01.1938 | | Luton Town | – | Scarborough | | 5:1 * |
| |
FA Cup 1935/36, Second Round Proper |
| 18.12.1935 | | Brighton & Hove Albion | – | Scarborough | | 3:0 * |
| |
FA Cup 1933/34, First Round Proper |
| 25.11.1933 | | North Shields | – | Scarborough | | 3:0 |
| |
FA Cup 1932/33, Second Round Proper |
| 10.12.1932 | | Southend United | – | Scarborough | | 4:1 |
| |
FA Cup 1930/31, Third Round Proper |
| 10.01.1931 | | Scarborough | – | Grimsby Town | | 1:2 |
| |
FA Cup 1928/29, Second Round Proper |
| 12.12.1928 | | Darlington | – | Scarborough | | 2:1 * |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Scarborough | – | Shankhouse | | 3:5 |
| |
