FA Cup 2022/23, Second Qualifying Round |
 | 20.09.2022 |  | Gainsborough Trinity | – | Long Eaton United | | 4:2 aet
(1:0, 1:1) * |
| Gainsborough |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Gainsborough Trinity | – | Loughborough University | | 3:1 (2:0) |
| Gainsborough |
FA Cup 2019/20, First Qualifying Round |
| 10.09.2019 | | Gainsborough Trinity | – | Banbury United | | 1:0 (0:0) * |
| Gainsborough |
FA Cup 2018/19, Second Qualifying Round |
| 22.09.2018 | | Halesowen Town | – | Gainsborough Trinity | | 0:3 (0:1) |
| Halesowen |
FA Cup 2018/19, First Qualifying Round |
| 11.09.2018 | | Gainsborough Trinity | – | Chasetown | | 8:2 (3:0) * |
| Gainsborough |
FA Cup 2017/18, Fourth Qualifying Round |
| 14.10.2017 | | Harrogate Town | – | Gainsborough Trinity | | 1:2 (1:0) |
| Harrogate |
FA Cup 2017/18, Third Qualifying Round |
| 03.10.2017 | | Gainsborough Trinity | – | Leamington | | 2:0 (0:0) * |
| Gainsborough |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Spennymoor Town | – | Gainsborough Trinity | | 1:2 (1:0) |
| Spennymoor |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 |  | Wrexham | – | Gainsborough Trinity | | 0:1 (0:0) |
| Wrexham |
FA Cup 2015/16, Third Qualifying Round |
| 10.10.2015 | | Droylsden | – | Gainsborough Trinity | | 3:4 (0:3) |
| Droylsden |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Gainsborough Trinity | – | Boston United | | 2:0 |
| Gainsborough |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Gainsborough Trinity | – | Marine | | 4:0 (0:0) |
| Gainsborough |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Gainsborough Trinity | – | Farsley AFC | | 4:1 (2:0) |
| Gainsborough |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | Gainsborough Trinity | – | Frickley Athletic | | 2:0 |
| |
FA Cup 2011/12, Second Qualifying Round |
| 04.10.2011 | | Gainsborough Trinity | – | AFC Fylde | | 2:1 aet
(1:1) * |
| Gainsborough |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Market Drayton Town | – | Gainsborough Trinity | | 1:2 |
| |
FA Cup 2007/08, Fourth Qualifying Round |
| 27.10.2007 | | Bradford Park Avenue | – | Gainsborough Trinity | | 0:4 (0:2) |
| |
FA Cup 2007/08, Third Qualifying Round |
| 13.10.2007 | | Gainsborough Trinity | – | Blyth Spartans | | 1:0 |
| |
FA Cup 2007/08, Second Qualifying Round |
| 29.09.2007 | | Gainsborough Trinity | – | Stocksbridge Park Steels | | 6:1 |
| |
FA Cup 2006/07, Fourth Qualifying Round |
| 28.10.2006 | | Gainsborough Trinity | – | Whitley Bay | | 2:0 (0:0) |
| |
FA Cup 2006/07, Third Qualifying Round |
| 14.10.2006 | | Woodley Sports | – | Gainsborough Trinity | | 0:2 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Ashton United | – | Gainsborough Trinity | | 0:2 |
| |
FA Cup 2005/06, Third Qualifying Round |
| 11.10.2005 | | Gainsborough Trinity | – | Leigh Railway Mechanics Institute | | 2:1 * |
| |
FA Cup 2005/06, Second Qualifying Round |
| 27.09.2005 | | Goole | – | Gainsborough Trinity | | 1:2 * |
| |
FA Cup 2003/04, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Farsley Celtic | | 3:0 * |
| |
FA Cup 2003/04, Third Qualifying Round |
| | | Droylsden | – | Gainsborough Trinity | | 0:2 (0:1) |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Gainsborough Trinity | – | Skelmersdale United | | 6:0 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Gainsborough Trinity | – | Frickley Athletic | | 3:2 |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Gainsborough Trinity | – | Dunston Federation Brewery | | 5:1 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Horden Colliery Welfare | – | Gainsborough Trinity | | 1:3 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Gainsborough Trinity | – | Eccleshill United | | 2:0 |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Halifax Town | | 2:1 |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Gainsborough Trinity | – | South Shields | | 3:2 |
| |
FA Cup 1997/98, Second Qualifying Round |
| | | Gateshead | – | Gainsborough Trinity | | 1:4 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Witton Albion | – | Gainsborough Trinity | | 0:5 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Gainsborough Trinity | – | Bridgnorth Town | | 2:1 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Gainsborough Trinity | – | Tow Law Town | | 2:0 * |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Gainsborough Trinity | – | Nantwich Town | | 5:0 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Gainsborough Trinity | – | Arnold Town | | 2:0 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Gainsborough Trinity | – | Redditch United | | 3:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Gainsborough Trinity | – | West Midlands Police | | 6:0 * |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Gainsborough Trinity | – | Pelsall Villa | | 4:2 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Gresley Rovers | – | Gainsborough Trinity | | 1:4 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Paget Rangers | – | Gainsborough Trinity | | 1:3 |
| |
FA Cup 1986/87, Third Qualifying Round |
| | | Grantham | – | Gainsborough Trinity | | 1:2 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Sutton Coldfield Town | – | Gainsborough Trinity | | 0:1 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Gainsborough Trinity | – | Alfreton Town | | 2:1 * |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Shepshed Charterhouse | – | Gainsborough Trinity | | 2:5 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Gainsborough Trinity | – | Oldswinford | | 3:0 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Hitchin Town | – | Gainsborough Trinity | | 0:1 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Bridgnorth Town | – | Gainsborough Trinity | | 1:4 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Gainsborough Trinity | – | Grantham | | 2:0 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Gainsborough Trinity | – | Ilkeston Town | | 6:0 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Gainsborough Trinity | – | Nuneaton Borough | | 2:0 * |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Gainsborough Trinity | – | Appleby Frodingham Athletic | | 2:1 * |
| |
FA Cup 1980/81, First Qualifying Round |
| | | March Town United | – | Gainsborough Trinity | | 1:2 |
| |
FA Cup 1980/81, Preliminary Round |
| | | Gainsborough Trinity | – | Heanor Town | | 3:1 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Brigg Town | – | Gainsborough Trinity | | 1:5 * |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Louth United | – | Gainsborough Trinity | | 1:2 * |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Enderby Town | – | Gainsborough Trinity | | 3:4 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Gainsborough Trinity | – | Ashby Institute | | 1:0 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Gainsborough Trinity | – | Mexborough Town | | 5:1 |
| |
FA Cup 1972/73, Third Qualifying Round |
| | | Gainsborough Trinity | – | Worksop Town | | 1:0 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Gainsborough Trinity | – | Barton Town | | 3:1 * |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Winterton Rangers | – | Gainsborough Trinity | | 1:3 |
| |
FA Cup 1970/71, Third Qualifying Round |
| | | Heanor Town | – | Gainsborough Trinity | | 0:2 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Alfreton Town | – | Gainsborough Trinity | | 1:2 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Worksop Town | – | Gainsborough Trinity | | 0:1 |
| |
FA Cup 1970/71, Preliminary Round |
| | | Gainsborough Trinity | – | Sutton Town | | 2:1 |
| |
FA Cup 1969/70, Third Qualifying Round |
| | | Gainsborough Trinity | – | Frickley Colliery | | 3:2 |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | Gainsborough Trinity | – | Worksop Town | | 2:1 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Thackley | – | Gainsborough Trinity | | 1:4 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Gainsborough Trinity | – | Denaby United | | 4:0 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Goole Town | | 1:0 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Farsley Celtic | – | Gainsborough Trinity | | 0:1 * |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Gainsborough Trinity | – | Denaby United | | 2:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Gainsborough Trinity | – | Ossett Albion | | 3:0 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Goole Town | – | Gainsborough Trinity | | 3:4 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Gainsborough Trinity | – | Denaby United | | 4:1 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Gainsborough Trinity | – | Retford Town | | 1:0 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Worksop Town | – | Gainsborough Trinity | | 1:3 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Norton Woodseats | – | Gainsborough Trinity | | 1:6 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Gainsborough Trinity | – | Stocksbridge Works | | 4:0 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Gainsborough Trinity | – | Worksop Town | | 2:1 * |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Denaby United | – | Gainsborough Trinity | | 1:2 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Gainsborough Trinity | – | Stocksbridge Works | | 3:1 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Gainsborough Trinity | – | Norton Woodseats | | 6:0 |
| |
FA Cup 1959/60, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Heanor Town | | 4:2 |
| |
FA Cup 1959/60, Third Qualifying Round |
| | | Gainsborough Trinity | – | Skegness Town | | 3:0 * |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Gainsborough Trinity | – | Bourne Town | | 4:1 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Gainsborough Trinity | – | Alford United | | 4:1 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Gainsborough Trinity | – | Brigg Town | | 6:2 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Grantham | – | Gainsborough Trinity | | 1:4 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Gainsborough Trinity | – | Louth United | | 4:2 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Worksop Town | | 2:1 * |
| |
FA Cup 1952/53, First Round Proper |
| 27.11.1952 | | Netherfield | – | Gainsborough Trinity | | 0:3 * |
| |
FA Cup 1952/53, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Ilkeston Town | | 5:1 |
| |
FA Cup 1951/52, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Creswell Colliery | | 5:2 |
| |
FA Cup 1950/51, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Brush Sports | | 3:1 |
| |
FA Cup 1948/49, First Round Proper |
| 27.11.1948 | | Gainsborough Trinity | – | Witton Albion | | 1:0 |
| |
FA Cup 1948/49, Fourth Qualifying Round |
| | | Norton Woodseats | – | Gainsborough Trinity | | 2:4 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Yorkshire Amateur | | 6:2 * |
| |
FA Cup 1945/46, First Round Proper |
| 24.11.1945 | | Gainsborough Trinity | – | Mansfield Town | | 4:2 |
| |
FA Cup 1945/46, Fourth Qualifying Round |
| | | Rawmarsh Welfare | – | Gainsborough Trinity | | 1:3 |
| |
FA Cup 1938/39, First Round Proper |
| 26.11.1938 | | Gainsborough Trinity | – | Gateshead | | 2:1 |
| |
FA Cup 1937/38, First Round Proper |
| 01.12.1937 | | Gainsborough Trinity | – | Port Vale | | 2:1 * |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | Gainsborough Trinity | – | Blyth Spartans | | 3:1 |
| |
FA Cup 1933/34, First Round Proper |
| 25.11.1933 | | Gainsborough Trinity | – | Altrincham | | 1:0 |
| |
FA Cup 1931/32, First Round Proper |
| 02.12.1931 | | Gainsborough Trinity | – | Crewe Alexandra | | 1:0 * |
| |
FA Cup 1930/31, First Round Proper |
| 29.11.1930 | | Gainsborough Trinity | – | Scunthorpe United | | 1:0 |
| |
FA Cup 1928/29, First Round Proper |
| 24.11.1928 | | Gainsborough Trinity | – | Crewe Alexandra | | 3:1 |
| |
FA Cup 1927/28, First Round Proper |
| 26.11.1927 | | Gainsborough Trinity | – | Stockton | | 6:0 |
| |
FA Cup 1912/13, First Round Proper |
| 18.01.1913 | | South Shields | – | Gainsborough Trinity | | 0:1 |
| |
FA Cup 1907/08, First Round Proper |
| 11.01.1908 | | Gainsborough Trinity | – | Watford | | 1:0 |
| |
FA Cup 1905/06, First Round Proper |
| 13.01.1906 | | Burslem Port Vale | – | Gainsborough Trinity | | 0:3 |
| |
FA Cup 1897/98, First Round Proper |
| 29.01.1898 | | Long Eaton Rangers | – | Gainsborough Trinity | | 0:1 |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Gainsborough Trinity | – | Boston | | 7:0 |
| |
FA Cup 1886/87, Second Round |
| 20.11.1886 | | Newcastle West End | – | Gainsborough Trinity | | 2:6 |
| |
FA Cup 1886/87, First Round |
| 30.10.1886 | | South Bank | – | Gainsborough Trinity | | 0:4 |
| |
FA Cup 1885/86, First Round |
| 24.10.1885 | | Gainsborough Trinity | – | Grantham | | 4:1 |
| |
