FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 |  | Plymouth Parkway | – | Dorchester Town | | 2:0 (1:0) |
| Plymouth |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Swindon Supermarine | – | Dorchester Town | | 1:0 (1:0) |
| Swindon |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Dorchester Town | – | Yate Town | | 1:3 (1:2) |
| Dorchester |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Christchurch | – | Dorchester Town | | 2:1 |
| Christchurch |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Blackfield & Langley | – | Dorchester Town | | 1:0 (0:0) |
| Blackfield |
FA Cup 2018/19, Second Qualifying Round |
| 22.09.2018 | | Tiverton Town | – | Dorchester Town | | 2:0 (1:0) |
| Tiverton |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | AFC Portchester | – | Dorchester Town | | 1:0 (0:0) |
| Portchester |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Dorchester Town | – | Banbury United | | 0:3 |
| Dorchester |
FA Cup 2015/16, First Qualifying Round |
| 15.09.2015 | | Cirencester Town | – | Dorchester Town | | 3:1 (1:1) * |
| Cirencester |
FA Cup 2014/15, Fourth Qualifying Round |
| 25.10.2014 | | Dorchester Town | – | Bristol Rovers | | 1:7 (0:2) |
| Dorchester |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Dorchester Town | – | Shortwood United | | 0:1 |
| Dorchester |
FA Cup 2012/13, Second Round Proper |
| 01.12.2012 | | Luton Town | – | Dorchester Town | | 2:1 (1:0) |
| Luton |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Dorchester Town | – | Weston-super-Mare | | 0:1 |
| |
FA Cup 2010/11, Third Qualifying Round |
| 09.10.2010 | | Havant & Waterlooville | – | Dorchester Town | | 4:1 |
| |
FA Cup 2009/10, Third Qualifying Round |
| 10.10.2009 | | Dorchester Town | – | Gloucester City | | 1:2 |
| |
FA Cup 2008/09, First Round Proper |
| 18.11.2008 | | Dorchester Town | – | Oxford United | | 1:3 aet
(1:0, 1:1) * |
| Dorchester |
FA Cup 2007/08, Second Qualifying Round |
| 01.10.2007 | | Paulton Rovers | – | Dorchester Town | | 2:0 * |
| |
FA Cup 2006/07, Third Qualifying Round |
| 14.10.2006 | | Dorchester Town | – | Lewes | | 0:4 |
| |
FA Cup 2005/06, Fourth Qualifying Round |
| 22.10.2005 | | Dorchester Town | – | Welling United | | 1:2 (1:0) |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 0:1 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Weston-Super-Mare | – | Dorchester Town | | 4:1 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Clevedon Town | – | Dorchester Town | | 2:0 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Bournemouth Amateurs | – | Dorchester Town | | 3:1 |
| |
FA Cup 2000/01, First Round Proper |
| 18.11.2000 | | Wigan Athletic | – | Dorchester Town | | 3:1 (2:1) |
| Wigan |
FA Cup 1999/00, Second Qualifying Round |
| | | Taunton Town | – | Dorchester Town | | 3:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Dorchester Town | – | Salisbury City | | 0:3 |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Dorchester Town | – | Tiverton Town | | 0:1 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Clevedon Town | – | Dorchester Town | | 4:1 |
| |
FA Cup 1995/96, First Round Proper |
| 11.11.1995 | | Oxford United | – | Dorchester Town | | 9:1 (2:0) |
| Oxford |
FA Cup 1994/95, Third Qualifying Round |
| | | Dorchester Town | – | Bashley | | 0:2 * |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Dorchester Town | – | Newbury Town | | 0:3 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Dorchester Town | – | AFC Lymington | | 2:4 * |
| |
FA Cup 1991/92, Fourth Qualifying Round |
| | | Hayes | – | Dorchester Town | | 1:0 |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Liskeard Athletic | – | Dorchester Town | | 5:1 |
| |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Gloucester City | – | Dorchester Town | | 1:0 |
| |
FA Cup 1988/89, Third Qualifying Round |
| | | Dorchester Town | – | Worcester City | | 1:2 * |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Cheltenham Town | – | Dorchester Town | | 4:1 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Forest Green Rovers | – | Dorchester Town | | 4:2 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Dorchester Town | – | Clandown | | 1:2 * |
| |
FA Cup 1984/85, Second Qualifying Round |
| |  | Merthyr Tydfil | – | Dorchester Town | | 3:0 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Dorchester Town | – | Wokingham Town | | 0:3 |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | AFC Totton | – | Dorchester Town | | 1:0 |
| |
FA Cup 1981/82, Second Round Proper |
| 15.12.1981 | | Bournemouth | – | Dorchester Town | | 2:1 * |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Gloucester City | – | Dorchester Town | | 1:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Dorchester Town | – | Barnstaple Town | | 1:3 * |
| |
FA Cup 1978/79, Third Qualifying Round |
| | | Yeovil Town | – | Dorchester Town | | 2:1 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Bath City | – | Dorchester Town | | 2:0 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Poole Town | – | Dorchester Town | | 2:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Bridport | – | Dorchester Town | | 4:3 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 1:3 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Dorchester Town | – | Bridgwater Town | | 0:1 * |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Andover | – | Dorchester Town | | 2:1 * |
| |
FA Cup 1971/72, Second Qualifying Round |
| | | Bridgwater Town | – | Dorchester Town | | 1:0 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Dorchester Town | – | Glastonbury | | 1:2 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Dorchester Town | – | Poole Town | | 2:5 |
| |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Dorchester Town | – | Salisbury | | 1:2 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Poole Town | – | Dorchester Town | | 1:0 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Portland United | – | Dorchester Town | | 4:1 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Dorchester Town | – | Salisbury | | 1:3 * |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 3:0 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Dorchester Town | – | Poole Town | | 0:3 |
| |
FA Cup 1961/62, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 2:0 * |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Chichester City | – | Dorchester Town | | 4:1 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Dorchester Town | – | Port Vale | | 1:2 |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 3:0 |
| |
FA Cup 1957/58, Second Round Proper |
| 07.12.1957 | | Plymouth Argyle | – | Dorchester Town | | 5:2 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Queens Park Rangers | – | Dorchester Town | | 4:0 |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Norwich City | – | Dorchester Town | | 4:0 |
| |
FA Cup 1954/55, Second Round Proper |
| 11.12.1954 | | Dorchester Town | – | York City | | 2:5 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Dorchester Town | – | Portland United | | 1:3 |
| |
FA Cup 1952/53, Fourth Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 1:5 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Dorchester Town | – | Portland United | | 2:3 * |
| |
FA Cup 1950/51, Fourth Qualifying Round |
| | | Dorchester Town | – | Glastonbury | | 1:4 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Cowes | – | Dorchester Town | | 5:1 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Dorchester Town | – | Ryde Sports | | 0:2 |
| |
