FA Cup 2023/24, Third Qualifying Round |
 | 30.09.2023 |  | Weymouth | – | Bath City | | 1:2 (0:1) |
| Weymouth |
FA Cup 2022/23, First Round Proper |
| 15.11.2022 | | AFC Wimbledon | – | Weymouth | | 3:1 (0:0) * |
| London |
FA Cup 2020/21, Fourth Qualifying Round |
| 24.10.2020 | | Weymouth | – | Oxford City | | 2:3 |
| Weymouth |
FA Cup 2019/20, Fourth Qualifying Round |
| 19.10.2019 | | Weymouth | – | Dover Athletic | | 1:2 (0:0) |
| Weymouth |
FA Cup 2018/19, First Qualifying Round |
| 11.09.2018 | | Banbury United | – | Weymouth | | 2:1 (1:0) * |
| Banbury |
FA Cup 2017/18, Third Qualifying Round |
| 30.09.2017 | | Chelmsford City | – | Weymouth | | 2:1 (0:0) |
| Chelmsford |
FA Cup 2016/17, Fourth Qualifying Round |
| 15.10.2016 | | Kidderminster Harriers | – | Weymouth | | 6:0 |
| Kidderminster |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Petersfield Town | – | Weymouth | | 3:1 (2:0) |
| Petersfield |
FA Cup 2014/15, Fourth Qualifying Round |
| 28.10.2014 | | Braintree Town | – | Weymouth | | 5:3 aet
(1:0, 3:3) * |
| Braintree |
FA Cup 2013/14, Fourth Qualifying Round |
| 26.10.2013 | | Weymouth | – | Braintree Town | | 1:2 (0:2) |
| Weymouth |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Basingstoke Town | – | Weymouth | | 3:1 |
| Basingstoke |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | AFC Totton | – | Weymouth | | 4:2 (2:0) |
| |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Swindon Supermarine | – | Weymouth | | 3:0 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Bishop's Cleeve | – | Weymouth | | 3:0 |
| |
FA Cup 2008/09, Fourth Qualifying Round |
| 25.10.2008 | | Weymouth | – | AFC Hornchurch | | 1:2 |
| |
FA Cup 2007/08, Second Round Proper |
| 01.12.2007 | | Cambridge United | – | Weymouth | | 1:0 (1:0) |
| Cambridge |
FA Cup 2006/07, First Round Proper |
| 21.11.2006 | | Bury | – | Weymouth | | 4:3 (2:3) * |
| Bury |
FA Cup 2005/06, First Round Proper |
| 14.11.2005 | | Weymouth | – | Nottingham Forest | | 0:2 (0:0) * |
| Weymouth |
FA Cup 2004/05, Third Qualifying Round |
| | | Thame United | – | Weymouth | | 2:1 * |
| |
FA Cup 2003/04, Second Qualifying Round |
| |  | Newport County | – | Weymouth | | 3:2 |
| |
FA Cup 2002/03, Third Qualifying Round |
| | | Tiverton Town | – | Weymouth | | 4:2 |
| |
FA Cup 2001/02, Fourth Qualifying Round |
| | | Weymouth | – | Hinckley United | | 1:2 (0:0) |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 0:1 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Gloucester City | – | Weymouth | | 2:1 * |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Welling United | – | Weymouth | | 3:2 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Tiverton Town | – | Weymouth | | 2:0 |
| |
FA Cup 1996/97, Third Qualifying Round |
| | | Cheltenham Town | – | Weymouth | | 1:0 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 2:3 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Torrington | – | Weymouth | | 2:0 |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Weymouth | – | Farnborough Town | | 1:4 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Bath City | – | Weymouth | | 2:0 |
| |
FA Cup 1991/92, Fourth Qualifying Round |
| | | Sutton United | – | Weymouth | | 3:0 * |
| |
FA Cup 1990/91, Third Qualifying Round |
| | | Weymouth | – | Bashley | | 2:3 * |
| |
FA Cup 1989/90, Third Qualifying Round |
| | | Exmouth Town | – | Weymouth | | 2:0 |
| |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Newport County | – | Weymouth | | 2:1 |
| |
FA Cup 1987/88, Fourth Qualifying Round |
| | | Weymouth | – | Yeovil Town | | 1:3 |
| |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Woking | – | Weymouth | | 1:0 |
| |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Chelmsford City | – | Weymouth | | 1:0 |
| |
FA Cup 1984/85, First Round Proper |
| 17.11.1984 | | Weymouth | – | Millwall | | 0:3 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Farnborough Town | – | Weymouth | | 3:2 * |
| |
FA Cup 1982/83, Third Round Proper |
| 08.01.1983 | | Cambridge United | – | Weymouth | | 1:0 |
| |
FA Cup 1981/82, First Round Proper |
| 24.11.1981 | | Northampton Town | – | Weymouth | | 6:2 * |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Swindon Town | – | Weymouth | | 3:2 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | Yeovil Town | – | Weymouth | | 2:1 |
| |
FA Cup 1978/79, First Round Proper |
| 29.11.1978 | | Weymouth | – | Aldershot | | 0:2 * |
| |
FA Cup 1977/78, First Round Proper |
| 30.11.1977 | | Weymouth | – | Gillingham | | 0:1 * |
| |
FA Cup 1976/77, First Round Proper |
| 02.12.1976 | | Hitchin Town | – | Weymouth | | 3:1 * |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Weymouth | – | Gillingham | | 0:2 |
| |
FA Cup 1974/75, First Round Proper |
| 09.12.1974 | | Peterborough United | – | Weymouth | | 3:0 * |
| Peterborough |
FA Cup 1973/74, First Round Proper |
| 24.11.1973 | | Weymouth | – | Merthyr Tydfil | | 0:1 |
| |
FA Cup 1972/73, Fourth Qualifying Round |
| | | Barnstaple Town | – | Weymouth | | 1:0 |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Cambridge United | – | Weymouth | | 2:1 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Southend United | – | Weymouth | | 7:0 |
| |
FA Cup 1969/70, First Round Proper |
| 19.11.1969 | | Weymouth | – | Northampton Town | | 1:3 (0:2) * |
| |
FA Cup 1968/69, Second Round Proper |
| 10.12.1968 | | Swansea Town | – | Weymouth | | 2:0 * |
| |
FA Cup 1967/68, First Round Proper |
| 09.12.1967 | | Weymouth | – | Orient | | 0:2 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Weymouth | – | Bath City | | 0:1 * |
| |
FA Cup 1965/66, First Round Proper |
| 17.11.1965 | | Weymouth | – | Bournemouth | | 1:4 * |
| |
FA Cup 1964/65, Second Round Proper |
| 05.12.1964 | | Bristol Rovers | – | Weymouth | | 4:1 |
| |
FA Cup 1963/64, First Round Proper |
| 21.11.1963 | | Bedford Town | – | Weymouth | | 1:0 * |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Weymouth | – | Poole Town | | 0:2 * |
| |
FA Cup 1961/62, Fourth Round Proper |
| 29.01.1962 | | Preston North End | – | Weymouth | | 2:0 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Weymouth | – | Torquay United | | 1:3 |
| |
FA Cup 1959/60, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 0:1 |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Weymouth | – | Coventry City | | 2:5 |
| |
FA Cup 1957/58, Fourth Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 2:1 * |
| |
FA Cup 1956/57, Second Round Proper |
| 08.12.1956 | | Southampton | – | Weymouth | | 3:2 |
| |
FA Cup 1955/56, Second Round Proper |
| 10.12.1955 | | Weymouth | – | Southend United | | 0:1 |
| |
FA Cup 1954/55, Fourth Qualifying Round |
| | | Frome Town | – | Weymouth | | 3:1 |
| |
FA Cup 1953/54, Second Round Proper |
| 12.12.1953 | | Leyton Orient | – | Weymouth | | 4:0 |
| |
FA Cup 1952/53, First Round Proper |
| 27.11.1952 | | Colchester United | – | Weymouth | | 4:0 * |
| |
FA Cup 1951/52, Second Round Proper |
| 15.12.1951 | | Bristol Rovers | – | Weymouth | | 2:0 |
| |
FA Cup 1950/51, Fourth Qualifying Round |
| | | Llanelli | – | Weymouth | | 5:0 |
| |
FA Cup 1949/50, Third Round Proper |
| 07.01.1950 | | Manchester United | – | Weymouth | | 4:0 |
| |
FA Cup 1948/49, Second Round Proper |
| 11.12.1948 | | Weymouth | – | Yeovil Town | | 0:4 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Newport IOW | – | Weymouth | | 5:2 |
| |
FA Cup 1926/27, First Round Proper |
| 01.12.1926 | | Reading | – | Weymouth | | 5:0 * |
| |
FA Cup 1925/26, First Round Proper |
| 28.11.1925 | | Weymouth | – | Newport County | | 0:1 |
| |
