FA Cup 2022/23, First Round Proper |
 | 05.11.2022 |  | Weymouth | – | AFC Wimbledon | | 1:1 (0:1) |
| Weymouth |
FA Cup 2021/22, Fourth Qualifying Round |
| 19.10.2021 | | Weymouth | – | Yeovil Town | | 1:1 aet
(0:1, 1:1),
pen. 1:2 * |
| Weymouth |
FA Cup 2021/22, Fourth Qualifying Round |
| 16.10.2021 | | Yeovil Town | – | Weymouth | | 1:1 (1:0) |
| Yeovil |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Weymouth | – | Banbury United | | 1:1 (1:0) |
| Weymouth |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Weymouth | – | Paulton Rovers | | 1:1 |
| Weymouth |
FA Cup 2014/15, Fourth Qualifying Round |
| 25.10.2014 | | Weymouth | – | Braintree Town | | 0:0 |
| Weymouth |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Weymouth | – | Bognor Regis Town | | 2:2 |
| Weymouth |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Totton & Eling | – | Weymouth | | 2:2 (1:1) |
| Totton |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Weymouth | – | Hungerford Town | | 3:3 (1:2) |
| Weymouth |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Weymouth | – | Taunton Town | | 0:0 |
| |
FA Cup 2007/08, Fourth Qualifying Round |
| 27.10.2007 | | Weymouth | – | Hitchin Town | | 1:1 (0:1) |
| |
FA Cup 2006/07, First Round Proper |
| 12.11.2006 | | Weymouth | – | Bury | | 2:2 (0:1) |
| Weymouth |
FA Cup 2005/06, First Round Proper |
| 05.11.2005 | | Nottingham Forest | – | Weymouth | | 1:1 (1:0) |
| Nottingham |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Weston-Super-Mare | – | Weymouth | | 2:2 |
| |
FA Cup 2004/05, Third Qualifying Round |
| | | Weymouth | – | Thame United | | 1:1 (0:1) |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Weymouth | – | Gloucester City | | 0:0 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Ryde Sports | – | Weymouth | | 1:1 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Fareham Town | – | Weymouth | | 1:1 |
| |
FA Cup 1991/92, Fourth Qualifying Round |
| | | Weymouth | – | Sutton United | | 1:1 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Weymouth | – | Barry Town |  | 1:1 |
| |
FA Cup 1990/91, Third Qualifying Round |
| | | Bashley | – | Weymouth | | 2:2 |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Swanage Town & Herston | – | Weymouth | | 1:1 |
| |
FA Cup 1987/88, Third Qualifying Round |
| | | Weymouth | – | Fareham Town | | 2:2 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Frome Town | – | Weymouth | | 2:2 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Weymouth | – | Farnborough Town | | 1:1 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Cheltenham Town | – | Weymouth | | 0:0 |
| |
FA Cup 1981/82, First Round Proper |
| 21.11.1981 | | Weymouth | – | Northampton Town | | 0:0 |
| |
FA Cup 1980/81, Fourth Qualifying Round |
| | | Weymouth | – | Taunton Town | | 0:0 |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Aldershot | – | Weymouth | | 1:1 |
| |
FA Cup 1977/78, First Round Proper |
| 26.11.1977 | | Gillingham | – | Weymouth | | 1:1 |
| |
FA Cup 1977/78, Fourth Qualifying Round |
| | | Worcester City | – | Weymouth | | 2:2 |
| |
FA Cup 1976/77, First Round Proper |
| 29.11.1976 | | Weymouth | – | Hitchin Town | | 3:3 aet * |
| |
FA Cup 1976/77, First Round Proper |
| 24.11.1976 | | Hitchin Town | – | Weymouth | | 2:2 aet * |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Weymouth | – | Hitchin Town | | 1:1 |
| |
FA Cup 1974/75, First Round Proper |
| 04.12.1974 | | Weymouth | – | Peterborough United | | 3:3 aet * |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Peterborough United | – | Weymouth | | 0:0 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Weymouth | – | Yeovil Town | | 2:2 aet * |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Yeovil Town | – | Weymouth | | 1:1 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Northampton Town | – | Weymouth | | 0:0 |
| |
FA Cup 1968/69, Second Round Proper |
| 07.12.1968 | | Weymouth | – | Swansea Town | | 1:1 |
| |
FA Cup 1968/69, Fourth Qualifying Round |
| | | Weymouth | – | Poole Town | | 1:1 |
| |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Weymouth | – | Bath City | | 1:1 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Bath City | – | Weymouth | | 2:2 |
| |
FA Cup 1965/66, First Round Proper |
| 13.11.1965 | | Bournemouth | – | Weymouth | | 0:0 |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Weymouth | – | Bideford | | 1:1 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Welton Rovers | – | Weymouth | | 1:1 |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Weymouth | – | Bedford Town | | 1:1 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Poole Town | – | Weymouth | | 0:0 |
| |
FA Cup 1961/62, Fourth Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 3:3 |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Weymouth | – | Salisbury | | 1:1 |
| |
FA Cup 1960/61, Third Qualifying Round |
| | | Weymouth | – | Poole Town | | 1:1 |
| |
FA Cup 1957/58, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 2:2 |
| |
FA Cup 1956/57, Fourth Qualifying Round |
| | | Chippenham Town | – | Weymouth | | 0:0 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Weymouth | – | Colchester United | | 1:1 |
| |
FA Cup 1951/52, Fourth Qualifying Round |
| | | Yeovil Town | – | Weymouth | | 1:1 |
| |
FA Cup 1949/50, First Round Proper |
| 26.11.1949 | | Weymouth | – | Aldershot | | 2:2 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Weymouth | – | Trowbridge Town | | 3:3 |
| |
FA Cup 1926/27, First Round Proper |
| 27.11.1926 | | Reading | – | Weymouth | | 4:4 |
| |
