FA Cup 2023/24, First Qualifying Round |
 | 05.09.2023 |  | Matlock Town | – | Gainsborough Trinity | | 5:2 (3:2) * |
| Matlock |
FA Cup 2022/23, Third Qualifying Round |
| 01.10.2022 | | Gainsborough Trinity | – | Worksop Town | | 0:1 (0:1) |
| Gainsborough |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Sporting Khalsa | – | Gainsborough Trinity | | 2:1 (0:0) |
| Willenhall |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | AFC Mansfield | – | Gainsborough Trinity | | 3:0 |
| Clipstone The Forest Town Stadium |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Rushall Olympic | – | Gainsborough Trinity | | 2:0 (1:0) |
| Walsall |
FA Cup 2018/19, Third Qualifying Round |
| 06.10.2018 | | Gainsborough Trinity | – | Blyth Spartans | | 1:2 (1:2) |
| Gainsborough |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Gainsborough Trinity | – | Slough Town | | 0:6 (0:1) |
| Gainsborough |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Altrincham | – | Gainsborough Trinity | | 3:2 |
| Altrincham |
FA Cup 2015/16, First Round Proper |
| 08.11.2015 | | Gainsborough Trinity | – | Shrewsbury Town | | 0:1 (0:0) |
| Gainsborough |
FA Cup 2014/15, Fourth Qualifying Round |
| 25.10.2014 | | Gateshead | – | Gainsborough Trinity | | 4:0 (1:0) |
| Gateshead |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Gainsborough Trinity | – | Rushall Olympic | | 0:3 |
| Gainsborough |
FA Cup 2012/13, Second Qualifying Round |
| 02.10.2012 | | Chester | – | Gainsborough Trinity | | 2:1 aet
(0:0, 1:1) * |
| Chester |
FA Cup 2011/12, Fourth Qualifying Round |
| 29.10.2011 | | A.F.C. Telford United | – | Gainsborough Trinity | | 5:0 (2:0) |
| Telford |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | United Of Manchester | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 2009/10, Third Qualifying Round |
| 10.10.2009 | | Nuneaton Town | – | Gainsborough Trinity | | 1:0 |
| |
FA Cup 2008/09, Second Qualifying Round |
| 27.09.2008 | | Halesowen Town | – | Gainsborough Trinity | | 3:0 |
| |
FA Cup 2007/08, First Round Proper |
| 11.11.2007 | | Gainsborough Trinity | – | Hartlepool United | | 0:6 (0:2) |
| Gainsborough |
FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | Gainsborough Trinity | – | Barnet | | 1:3 (0:1) |
| Gainsborough |
FA Cup 2005/06, Fourth Qualifying Round |
| 22.10.2005 | | Gainsborough Trinity | – | York City | | 0:4 (0:2) |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Gainsborough Trinity | – | Halesowen Town | | 2:3 |
| |
FA Cup 2003/04, First Round Proper |
| 08.11.2003 | | Brentford | – | Gainsborough Trinity | | 7:1 (1:0) |
| Brentford |
FA Cup 2002/03, Third Qualifying Round |
| | | Vauxhall Motors | – | Gainsborough Trinity | | 6:1 |
| |
FA Cup 2001/02, Third Qualifying Round |
| | | Worksop Town | – | Gainsborough Trinity | | 4:0 (2:0) |
| |
FA Cup 2000/01, Third Qualifying Round |
| | | Whitley Bay | – | Gainsborough Trinity | | 2:0 * |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Gainsborough Trinity | – | Droylsden | | 1:2 * |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Hyde United | – | Gainsborough Trinity | | 4:0 |
| |
FA Cup 1997/98, First Round Proper |
| 25.11.1997 | | Gainsborough Trinity | – | Lincoln City | | 2:3 (2:3) * |
| Gainsborough |
FA Cup 1996/97, Third Qualifying Round |
| | | Leek Town | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Morecambe | – | Gainsborough Trinity | | 6:2 |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Gainsborough Trinity | – | Telford United | | 0:3 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Buxton | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1992/93, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Altrincham | | 0:2 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Lincoln United | – | Gainsborough Trinity | | 3:1 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Frickley Athletic | – | Gainsborough Trinity | | 4:3 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Gainsborough Trinity | – | Sutton Coldfield Town | | 1:2 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Gresley Rovers | – | Gainsborough Trinity | | 3:1 * |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Gainsborough Trinity | – | Matlock Town | | 0:3 * |
| |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Boston United | – | Gainsborough Trinity | | 6:0 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Gainsborough Trinity | – | Bromsgrove Rovers | | 1:2 * |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Nuneaton Borough | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Gainsborough Trinity | – | Blackpool | | 0:2 |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Shepshed Charterhouse | – | Gainsborough Trinity | | 3:0 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Gainsborough Trinity | – | Boston | | 1:2 * |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Corby Town | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Skegness Town | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1978/79, Third Qualifying Round |
| | | Boston United | – | Gainsborough Trinity | | 3:0 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Brigg Town | – | Gainsborough Trinity | | 1:0 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Emley | – | Gainsborough Trinity | | 4:1 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Frickley Colliery | – | Gainsborough Trinity | | 3:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Matlock Town | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Gainsborough Trinity | – | Sutton Town | | 1:2 |
| |
FA Cup 1972/73, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Grantham | | 1:2 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Gainsborough Trinity | – | Lincoln United | | 2:3 |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Grantham | – | Gainsborough Trinity | | 2:1 * |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Grantham | – | Gainsborough Trinity | | 5:0 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Frickley Colliery | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Farsley Celtic | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Gainsborough Trinity | – | Colchester United | | 0:1 |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Burton Albion | – | Gainsborough Trinity | | 3:2 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Gainsborough Trinity | – | Goole Town | | 1:3 |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Heanor Town | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Buxton | – | Gainsborough Trinity | | 4:1 * |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Worksop Town | – | Gainsborough Trinity | | 4:3 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Gainsborough Trinity | – | Denaby United | | 0:3 |
| |
FA Cup 1959/60, First Round Proper |
| 18.11.1959 | | Gainsborough Trinity | – | Doncaster Rovers | | 0:1 * |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Gainsborough Trinity | – | Boston United | | 1:3 * |
| |
FA Cup 1957/58, Second Qualifying Round |
| | | Alford United | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1956/57, Fourth Qualifying Round |
| | | Goole Town | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1955/56, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Skegness Town | | 0:2 * |
| |
FA Cup 1954/55, Fourth Qualifying Round |
| | | Selby Town | – | Gainsborough Trinity | | 4:2 |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Gainsborough Trinity | – | Chesterfield | | 1:4 |
| |
FA Cup 1952/53, Second Round Proper |
| 06.12.1952 |  | Newport County | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Witton Albion | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Gainsborough Trinity | – | Plymouth Argyle | | 0:3 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Grantham | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1948/49, Second Round Proper |
| 11.12.1948 | | Walsall | – | Gainsborough Trinity | | 4:3 |
| |
FA Cup 1947/48, Fourth Qualifying Round |
| | | Scunthorpe United | – | Gainsborough Trinity | | 4:2 |
| |
FA Cup 1946/47, First Round Proper |
| 30.11.1946 | | Gainsborough Trinity | – | Darlington | | 1:2 |
| |
FA Cup 1945/46, First Round Proper |
| 17.11.1945 | | Mansfield Town | – | Gainsborough Trinity | | 3:0 |
| |
FA Cup 1938/39, Second Round Proper |
| 10.12.1938 | | Gainsborough Trinity | – | Doncaster Rovers | | 0:1 |
| |
FA Cup 1937/38, Second Round Proper |
| 11.12.1937 | | Yeovil & Petter's United | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1935/36, Second Round Proper |
| 14.12.1935 | | Dartford | – | Gainsborough Trinity | | 4:0 |
| |
FA Cup 1933/34, Second Round Proper |
| 09.12.1933 | | Gainsborough Trinity | – | Aldershot | | 0:2 |
| |
FA Cup 1932/33, First Round Proper |
| 26.11.1932 | | Doncaster Rovers | – | Gainsborough Trinity | | 4:1 |
| |
FA Cup 1931/32, Second Round Proper |
| 12.12.1931 | | Gainsborough Trinity | – | Watford | | 2:5 |
| |
FA Cup 1930/31, Second Round Proper |
| 13.12.1930 | | Gainsborough Trinity | – | Southport | | 0:4 |
| |
FA Cup 1929/30, First Round Proper |
| 04.12.1929 | | Port Vale | – | Gainsborough Trinity | | 5:0 * |
| |
FA Cup 1928/29, Second Round Proper |
| 08.12.1928 | | Gainsborough Trinity | – | Chesterfield | | 2:3 |
| |
FA Cup 1927/28, Second Round Proper |
| 10.12.1927 | | Gainsborough Trinity | – | Lincoln City | | 0:2 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | Leeds City | – | Gainsborough Trinity | | 4:2 |
| |
FA Cup 1912/13, Second Round Proper |
| 01.02.1913 | | Burnley | – | Gainsborough Trinity | | 4:1 |
| |
FA Cup 1911/12, First Round Proper |
| 13.01.1912 | | West Ham United | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1910/11, First Round Proper |
| 14.01.1911 | | Liverpool | – | Gainsborough Trinity | | 3:2 |
| |
FA Cup 1909/10, First Round Proper |
| 19.01.1910 | | Southend United | – | Gainsborough Trinity | | 1:0 * |
| |
FA Cup 1908/09, First Round Proper |
| 16.01.1909 | | Brentford | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1907/08, Second Round Proper |
| 10.02.1908 | | Stoke | – | Gainsborough Trinity | | 3:1 * |
| |
FA Cup 1906/07, First Round Proper |
| 16.01.1907 | | Luton Town | – | Gainsborough Trinity | | 2:1 * |
| |
FA Cup 1905/06, Second Round Proper |
| 07.02.1906 | | Sunderland | – | Gainsborough Trinity | | 3:0 * |
| |
FA Cup 1904/05, Intermediate Round |
| 14.01.1905 | | Grimsby Town | – | Gainsborough Trinity | | 2:0 |
| |
FA Cup 1903/04, Intermediate Round |
| 12.12.1903 | | Reading | – | Gainsborough Trinity | | 1:0 |
| |
FA Cup 1897/98, Second Round Proper |
| 12.02.1898 | | Nottingham Forest | – | Gainsborough Trinity | | 4:0 |
| |
FA Cup 1887/88, Second Round |
| 05.11.1887 | | Lincoln City | – | Gainsborough Trinity | | 2:1 |
| |
FA Cup 1886/87, Third Round |
| 24.01.1887 | | Lincoln City | – | Gainsborough Trinity | | 1:0 * |
| |
FA Cup 1885/86, Second Round |
| 21.11.1885 | | Gainsborough Trinity | – | Middlesbrough | | 1:2 |
| |
