FA Cup 2023/24, Second Qualifying Round |
 | 16.09.2023 | | Highworth Town | – | Weymouth | | 1:3 (0:1) |
| Highworth |
FA Cup 2022/23, Fourth Qualifying Round |
| 15.10.2022 | | Havant & Waterlooville | – | Weymouth | | 1:2 (1:1) |
| Havant |
FA Cup 2022/23, Third Qualifying Round |
| 01.10.2022 | | Weymouth | – | Welling United | | 3:0 (2:0) |
| Weymouth |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Winchester City | – | Weymouth | | 1:3 (1:3) |
| Winchester |
FA Cup 2019/20, Third Qualifying Round |
| 05.10.2019 | | Weymouth | – | St Albans City | | 4:1 (2:0) |
| Weymouth |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Sholing | – | Weymouth | | 0:3 (0:2) |
| Southampton |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Weymouth | – | Chippenham Town | | 2:0 (1:0) |
| Weymouth |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Odd Down | – | Weymouth | | 0:5 (0:1) |
| Bath |
FA Cup 2016/17, Third Qualifying Round |
| 01.10.2016 | | Weymouth | – | Brimscombe & Thrupp | | 6:0 |
| Weymouth |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Weymouth | – | Gosport Borough | | 3:2 |
| Weymouth |
FA Cup 2016/17, First Qualifying Round |
| 06.09.2016 | | Weymouth | – | Paulton Rovers | | 2:1 * |
| Weymouth |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Billericay Town | – | Weymouth | | 0:1 (0:1) |
| Billericay |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Weymouth | – | Bideford | | 4:1 (2:1) |
| Weymouth |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Mangotsfield United | – | Weymouth | | 0:3 (0:2) |
| Mangotsfield |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Cirencester Town | – | Weymouth | | 1:2 (0:1) |
| Cirencester |
FA Cup 2013/14, Second Qualifying Round |
| 01.10.2013 | | Bognor Regis Town | – | Weymouth | | 1:4 * |
| Bognor Regis |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Fareham Town | – | Weymouth | | 0:1 |
| Fareham |
FA Cup 2012/13, First Qualifying Round |
| 11.09.2012 | | Weymouth | – | Totton & Eling | | 3:0 (3:0) * |
| Weymouth |
FA Cup 2011/12, Second Qualifying Round |
| 04.10.2011 | | Hungerford Town | – | Weymouth | | 1:3 (1:2) * |
| |
FA Cup 2011/12, First Qualifying Round |
| 19.09.2011 | | Taunton Town | – | Weymouth | | 1:3 * |
| |
FA Cup 2010/11, First Qualifying Round |
| 11.09.2010 | | Taunton Town | – | Weymouth | | 1:2 |
| |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Eastbourne Borough | – | Weymouth | | 0:4 (0:0) |
| |
FA Cup 2007/08, Fourth Qualifying Round |
| 30.10.2007 | | Hitchin Town | – | Weymouth | | 0:1 (0:1) * |
| |
FA Cup 2006/07, Fourth Qualifying Round |
| 28.10.2006 | | Hungerford Town | – | Weymouth | | 0:3 (0:2) |
| |
FA Cup 2005/06, Fourth Qualifying Round |
| 22.10.2005 | | Weymouth | – | Cambridge United | | 2:1 (2:1) |
| |
FA Cup 2005/06, Third Qualifying Round |
| 08.10.2005 | | Weymouth | – | Bath City | | 1:0 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 27.09.2005 | | Weymouth | – | Weston-Super-Mare | | 1:0 * |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 0:1 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Chippenham Town | – | Weymouth | | 1:4 |
| |
FA Cup 2001/02, Third Qualifying Round |
| | | Weymouth | – | Crawley Town | | 3:1 (0:1) |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Highworth Town | – | Weymouth | | 0:3 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Merthyr Tydfil | – | Weymouth | | 0:2 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Weymouth | – | Abingdon Town | | 1:0 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Weymouth | – | Camberley Town | | 2:0 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Weymouth | – | Waterlooville | | 1:0 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Weymouth | – | Ryde Sports | | 2:1 * |
| |
FA Cup 1995/96, Preliminary Round |
| | | Weymouth | – | Fareham Town | | 3:2 * |
| |
FA Cup 1993/94, Third Qualifying Round |
| | | Weymouth | – | Barnstaple Town | | 2:1 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Weymouth | – | Elmore | | 3:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Chippenham Town | – | Weymouth | | 0:5 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Weymouth | – | Truro City | | 3:2 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Weymouth | – | Saltash United | | 1:0 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Weymouth | – | Cheltenham Town | | 4:0 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Barry Town | – | Weymouth | | 2:3 * |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Wimborne Town | – | Weymouth | | 1:2 |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Weymouth | – | Swanage Town & Herston | | 2:1 * |
| |
FA Cup 1990/91, First Qualifying Round |
| | | St Blazey | – | Weymouth | | 0:2 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Weymouth | – | St Blazey | | 2:0 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Weymouth | – | Barnstaple Town | | 2:0 |
| |
FA Cup 1988/89, Third Qualifying Round |
| | | Weymouth | – | Forest Green Rovers | | 3:0 |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Weston-Super-Mare | – | Weymouth | | 0:1 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Trowbridge Town | – | Weymouth | | 1:2 |
| |
FA Cup 1987/88, Third Qualifying Round |
| | | Fareham Town | – | Weymouth | | 1:2 * |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Weymouth | – | Radstock Town | | 3:0 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Weymouth | – | Frome Town | | 3:0 * |
| |
FA Cup 1985/86, Fourth Qualifying Round |
| | | Ton Pentre | – | Weymouth | | 1:3 |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Weymouth | – | Worcester City | | 3:1 |
| |
FA Cup 1982/83, Second Round Proper |
| 11.12.1982 | | Cardiff City | – | Weymouth | | 2:3 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Weymouth | – | Maidstone United | | 4:3 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Weymouth | – | Cheltenham Town | | 4:0 * |
| |
FA Cup 1981/82, Fourth Qualifying Round |
| | | Weymouth | – | Farnborough Town | | 3:0 |
| |
FA Cup 1980/81, Fourth Qualifying Round |
| | | Taunton Town | – | Weymouth | | 0:3 * |
| |
FA Cup 1978/79, Fourth Qualifying Round |
| | | Taunton Town | – | Weymouth | | 0:2 |
| |
FA Cup 1977/78, Fourth Qualifying Round |
| | | Weymouth | – | Worcester City | | 2:1 * |
| |
FA Cup 1976/77, Fourth Qualifying Round |
| | | Poole Town | – | Weymouth | | 2:3 |
| |
FA Cup 1975/76, Fourth Qualifying Round |
| | | Salisbury | – | Weymouth | | 4:5 |
| |
FA Cup 1974/75, Fourth Qualifying Round |
| | | Minehead | – | Weymouth | | 0:3 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Poole Town | – | Weymouth | | 0:3 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Weymouth | – | Welton Rovers | | 7:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 1:3 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Yeovil Town | – | Weymouth | | 0:1 * |
| |
FA Cup 1973/74, Third Qualifying Round |
| | | Taunton Town | – | Weymouth | | 1:2 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Weymouth | – | Salisbury | | 2:0 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Poole Town | – | Weymouth | | 0:3 |
| |
FA Cup 1971/72, Fourth Qualifying Round |
| | | Weymouth | – | Bideford | | 3:1 |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Weymouth | – | Bideford | | 3:0 |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Salisbury | – | Weymouth | | 0:1 |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Weymouth | – | Yeovil Town | | 2:1 |
| |
FA Cup 1968/69, Fourth Qualifying Round |
| | | Poole Town | – | Weymouth | | 0:1 * |
| |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Bath City | – | Weymouth | | 0:1 * |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Bideford | – | Weymouth | | 1:3 * |
| |
FA Cup 1964/65, First Round Proper |
| 18.11.1964 | | Weymouth | – | Welton Rovers | | 4:3 * |
| |
FA Cup 1964/65, Fourth Qualifying Round |
| | | Weymouth | – | Fareham Town | | 3:2 |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 3:0 |
| |
FA Cup 1961/62, Third Round Proper |
| 06.01.1962 | | Morecambe | – | Weymouth | | 0:1 |
| |
FA Cup 1961/62, Second Round Proper |
| 25.11.1961 | | Weymouth | – | Newport County | | 1:0 |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Weymouth | – | Barnet | | 1:0 |
| |
FA Cup 1961/62, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 2:0 * |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Salisbury | – | Weymouth | | 0:2 * |
| |
FA Cup 1960/61, Third Qualifying Round |
| | | Poole Town | – | Weymouth | | 3:4 * |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Weymouth | – | Warminster Town | | 5:1 |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Weymouth | – | Dorchester Town | | 3:0 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Weymouth | – | Shrewsbury Town | | 1:0 |
| |
FA Cup 1956/57, Fourth Qualifying Round |
| | | Weymouth | – | Chippenham Town | | 4:1 * |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Weymouth | – | Salisbury | | 3:2 |
| |
FA Cup 1955/56, Fourth Qualifying Round |
| | | Poole Town | – | Weymouth | | 2:3 |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Weymouth | – | Bedford Town | | 2:0 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Chippenham Town | – | Weymouth | | 2:4 |
| |
FA Cup 1952/53, Fourth Qualifying Round |
| | | Dorchester Town | – | Weymouth | | 1:5 |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Brush Sports | – | Weymouth | | 2:3 |
| |
FA Cup 1951/52, Fourth Qualifying Round |
| | | Weymouth | – | Yeovil Town | | 2:1 * |
| |
FA Cup 1949/50, Second Round Proper |
| 10.12.1949 | | Weymouth | – | Hereford United | | 2:1 |
| |
FA Cup 1949/50, First Round Proper |
| 30.11.1949 | | Aldershot | – | Weymouth | | 2:3 * |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Trowbridge Town | – | Weymouth | | 1:2 * |
| |
FA Cup 1949/50, Third Qualifying Round |
| | | Cowes | – | Weymouth | | 1:5 |
| |
FA Cup 1949/50, Second Qualifying Round |
| | | Weymouth | – | Poole Town | | 4:0 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Ryde Sports | – | Weymouth | | 2:6 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Weymouth | – | Totton | | 6:3 |
| |
FA Cup 1948/49, First Round Proper |
| 27.11.1948 | | Weymouth | – | Chelmsford City | | 2:1 |
| |
FA Cup 1948/49, Fourth Qualifying Round |
| | | Weymouth | – | Trowbridge Town | | 2:0 |
| |
FA Cup 1948/49, Third Qualifying Round |
| | | Weymouth | – | Poole Town | | 4:2 |
| |
FA Cup 1948/49, Second Qualifying Round |
| | | Longfleet St Mary's | – | Weymouth | | 0:4 |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Newport IOW | – | Weymouth | | 2:4 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Weymouth | – | Andover | | 3:0 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Weymouth | – | Bournemouth Amateurs | | 8:3 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Weymouth | – | Longfleet St Mary's | | 4:1 |
| |
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