FA Cup 2021/22, Extra Preliminary Round |
 | 07.08.2021 | | Bridport | – | Fleet Town | | 1:2 (1:0) |
| Bridport |
FA Cup 2020/21, Extra Preliminary Round |
| 02.09.2020 | | Willand Rovers | – | Bridport | | 2:1 |
| Willand |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Bitton | – | Bridport | | 2:1 |
| Bitton |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Bridport | – | Tiverton Town | | 0:1 (0:1) |
| Bridport |
FA Cup 2017/18, Third Qualifying Round |
| 30.09.2017 | | St Albans City | – | Bridport | | 2:1 (2:0) |
| St Albans |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Bridport | – | Alresford Town | | 1:2 |
| Bridport |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Bridport | – | Larkhall Athletic | | 2:5 (1:4) |
| Bridport |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Bridport | – | Highworth Town | | 2:3 |
| Bridport |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Bridport | – | Merthyr Town | | 2:3 (1:2) |
| Bridport |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Buckland Athletic | – | Bridport | | 2:1 |
| |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Horndean | – | Bridport | | 3:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Bridport | – | Clevedon Town | | 0:6 |
| |
FA Cup 2009/10, First Qualifying Round |
| 15.09.2009 | | Bridport | – | Truro City | | 0:7 * |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Clevedon Town | – | Bridport | | 4:1 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Bridport | – | Welton Rovers | | 0:5 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Tavistock | – | Bridport | | 4:2 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Bridport | – | Falmouth Town | | 0:3 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Bridport | – | Bath City | | 1:4 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Mangotsfield United | – | Bridport | | 4:3 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Bridport | – | Taunton Town | | 2:3 |
| |
FA Cup 2000/01, Extra Preliminary Round |
| | | Wimborne Town | – | Bridport | | 2:0 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Bridport | – | Christchurch | | 2:4 * |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Bridgwater Town | – | Bridport | | 1:0 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Bridport | – | Buckingham Town | | 1:2 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Bridport | – | Clevedon Town | | 0:1 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Bridport | – | Merthyr Tydfil | | 0:3 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Bridport | – | Backwell United | | 1:2 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Bridport | – | Elmore | | 2:3 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Bridport | – | Wimborne Town | | 2:3 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Liskeard Athletic | – | Bridport | | 3:1 * |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Bognor Regis Town | – | Bridport | | 3:1 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Glastonbury | – | Bridport | | 2:1 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Bridport | – | Dorchester Town | | 0:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Bridport | – | Bath City | | 0:3 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Bridport | – | Minehead | | 2:4 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Bridport | – | Frome Town | | 0:3 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Bridport | – | Poole Town | | 1:6 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Bridport | – | Salisbury | | 0:1 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Frome Town | – | Bridport | | 4:2 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Bridgwater Town | – | Bridport | | 1:0 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Glastonbury | – | Bridport | | 2:0 * |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | Minehead | – | Bridport | | 2:0 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Bridport | – | Frome Town | | 1:4 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Portland United | – | Bridport | | 3:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Poole Town | – | Bridport | | 7:0 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Poole Town | – | Bridport | | 3:2 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Poole Town | – | Bridport | | 2:0 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Dorchester Town | – | Bridport | | 1:0 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Bridport | – | Portland United | | 1:5 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Portland United | – | Bridport | | 4:3 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Poole Town | – | Bridport | | 6:3 |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Poole Town | – | Bridport | | 4:0 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Bridport | – | Salisbury | | 2:5 |
| |
FA Cup 1957/58, Third Qualifying Round |
| | | Portland United | – | Bridport | | 2:1 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Poole Town | – | Bridport | | 3:0 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Poole Town | – | Bridport | | 3:1 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Portland United | – | Bridport | | 4:2 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Bournemouth Gasworks Athletic | – | Bridport | | 8:0 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Bridport | – | Dorchester Town | | 0:2 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Bournemouth Gasworks Athletic | – | Bridport | | 3:1 * |
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