FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 | | Gainsborough Trinity | – | Matlock Town | | 1:1 (1:0) |
| Gainsborough |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Long Eaton United | – | Gainsborough Trinity | | 1:1 (1:0) |
| Long Eaton |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Banbury United | – | Gainsborough Trinity | | 2:2 (0:1) |
| Banbury |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Chasetown | – | Gainsborough Trinity | | 1:1 (0:0) |
| Chasetown |
FA Cup 2017/18, Third Qualifying Round |
| 30.09.2017 | | Leamington | – | Gainsborough Trinity | | 0:0 |
| Royal Leamington Spa |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Gainsborough Trinity | – | Chester | | 1:1 |
| Gainsborough |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | AFC Fylde | – | Gainsborough Trinity | | 2:2 (1:2) |
| |
FA Cup 2005/06, Third Qualifying Round |
| 08.10.2005 | | Leigh Railway Mechanics Institute | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Gainsborough Trinity | – | Goole AFC | | 2:2 |
| |
FA Cup 2003/04, Fourth Qualifying Round |
| | | Farsley Celtic | – | Gainsborough Trinity | | 1:1 (0:1) |
| |
FA Cup 2000/01, Third Qualifying Round |
| | | Gainsborough Trinity | – | Whitley Bay | | 0:0 |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Droylsden | – | Gainsborough Trinity | | 2:2 |
| |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Lincoln City | – | Gainsborough Trinity | | 1:1 (1:0) |
| Lincoln |
FA Cup 1996/97, First Qualifying Round |
| | | Tow Law Town | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | West Midlands Police | – | Gainsborough Trinity | | 0:0 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Gainsborough Trinity | – | Gresley Rovers | | 2:2 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Matlock Town | – | Gainsborough Trinity | | 3:3 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Alfreton Town | – | Gainsborough Trinity | | 0:0 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Bromsgrove Rovers | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Gainsborough Trinity | – | Bridgnorth Town | | 1:1 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Nuneaton Borough | – | Gainsborough Trinity | | 3:3 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Appleby Frodingham Athletic | – | Gainsborough Trinity | | 0:0 aet * |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Gainsborough Trinity | – | Appleby Frodingham Athletic | | 2:2 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Boston | – | Gainsborough Trinity | | 0:0 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Gainsborough Trinity | – | Brigg Town | | 1:1 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Gainsborough Trinity | – | Louth United | | 1:1 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Barton Town | – | Gainsborough Trinity | | 2:2 |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Grantham | | 3:3 aet * |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Grantham | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Gainsborough Trinity | – | Farsley Celtic | | 1:1 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Gainsborough Trinity | – | Buxton | | 0:0 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Worksop Town | – | Gainsborough Trinity | | 0:0 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Doncaster Rovers | – | Gainsborough Trinity | | 3:3 |
| |
FA Cup 1959/60, Third Qualifying Round |
| | | Skegness Town | – | Gainsborough Trinity | | 0:0 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Gainsborough Trinity | – | Boston United | | 2:2 aet * |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Boston United | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1955/56, Fourth Qualifying Round |
| | | Skegness Town | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Worksop Town | – | Gainsborough Trinity | | 2:2 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Gainsborough Trinity | – | Netherfield | | 1:1 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Yorkshire Amateur | – | Gainsborough Trinity | | 3:3 |
| |
FA Cup 1937/38, First Round Proper |
| 27.11.1937 | | Port Vale | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1931/32, First Round Proper |
| 28.11.1931 | | Crewe Alexandra | – | Gainsborough Trinity | | 2:2 |
| |
FA Cup 1929/30, First Round Proper |
| 30.11.1929 | | Gainsborough Trinity | – | Port Vale | | 0:0 |
| |
FA Cup 1909/10, First Round Proper |
| 15.01.1910 | | Gainsborough Trinity | – | Southend United | | 1:1 |
| |
FA Cup 1907/08, Second Round Proper |
| 05.02.1908 | | Gainsborough Trinity | – | Stoke | | 2:2 aet * |
| |
FA Cup 1907/08, Second Round Proper |
| 01.02.1908 | | Stoke | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1906/07, First Round Proper |
| 12.01.1907 | | Gainsborough Trinity | – | Luton Town | | 0:0 |
| |
FA Cup 1905/06, Second Round Proper |
| 03.02.1906 | | Sunderland | – | Gainsborough Trinity | | 1:1 |
| |
FA Cup 1886/87, Third Round |
| 11.12.1886 | | Gainsborough Trinity | – | Lincoln City | | 2:2 |
| |
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