League and League Cup History

Key - * - After Extra Time; # - Shared; R - Replay; P - Penalties
Season
League Winners
League Runners Up
League Cup Winners
League Cup Runners Up
Cup Score
2020/21
No Competition as a result of COVID-19
Merley Cobham Sports
Hamworthy Recreation
3 - 1
2019/20
No Competition as a result of COVID-19
No Competition as a result of COVID-19
2018/19
Hamworthy Recreation
Westland Sports
Merley Cobham Sports
Westland Sports
3 - 2
2017/18
Hamworthy Recreation
Westland Sports
Westland Sports
Hamworthy Recreation
2 - 0
2016/17
Holt United
Balti Sports
Swanage Town & Herston
Gillingham Town Res
2 - 0
2015/16
Shaftesbury Town
Hamworthy Recreation
Merley Cobham Sports
Sherborne Town Res
2 - 1
2014/15
Hamworthy Recreation
Portland Utd
Hamworthy Recreation
Mere Town
3 - 0
2013/14
Portland Utd
Weymouth Res
Hamworthy Recreation
Portland Utd
0 - 0
2012/13
Portland Utd
Wincanton Town
Holt Utd
Portland Utd
1 - 0
2011/12
Westland Sports
Hamworthy Recreation
Westland Sports
Hamworthy Recreation
2 - 2 *
2010/11
Hamworthy Recreation
Weymouth Res
Weymouth Res
Merley Cobham Sports
2 - 2 *
2009/10
Hamworthy Recreation
Chickerell Utd
Swanage Town & Herston
Westland Sports
3 - 0
2008/09
Portland Utd
Poole Borough
Portland Utd
Chickerell Utd
2 - 2 *
2007/08
Portland Utd
Gillingham Town
Hamworthy Recreation
Westland Sports
3 - 0
2006/07
Westland Sports
Holt Utd
Hamworthy Recreation
Portland Utd
1 - 1 *
2005/06
Holt Utd
Sherborne Town
Holt Utd
Dorchester Utd Res
2 - 1 *
2004/05
Hamworthy Recreation
Poole Borough
Poole Borough
Holt Utd
2 - 1
2003/04
Hamworthy Utd
Dorchester Town Res
Dorchester Town Res
Gillingham Town
1 - 0
2002/03
Hamworthy Utd
Gillingham Town
Holt Utd
Hamworthy Recreation
4 - 0
2001/02
Hamworthy Recreation
Sherborne Town
Gillingham Town
Westland Sports
2 - 1 *
2000/01
Hamworthy Recreation
Portland Utd
Hamworthy Recreation
Hamworthy Utd
2 - 0
1999/00
Portland Utd
Dorchester Town Res
Portland Utd
Gillingham Town
4 - 3 *
1998/99
Portland Utd
Parley Sports
Portland Utd
Parley Sports
3 - 0
1997/98
Sturminster Marshall
Portland Utd
Portland Utd
Westland Sports
3 - 0
1996/97
Shaftesbury
Bounemouth Sports
Bournemouth Sports
Hamworthy Engineering
3 - 2 *
1995/96
Hamworthy Engineering
Bridport Res
Sturminster Newton
Sherborne Town
2- 1
1994/95
Hamworthy Engineering
Bournemouth Sports
Shaftesbury
Hamworthy Engineering
4 - 2
1993/94
Hamworthy Engineering
Westland Sports
Westland Sports
Sherborne Town
3 - 2
1992/93
Westland Sports
Sherborne Town
Westland Sports
Portland Utd
4 - 2
1991/92
Blandford Utd
Westland Sports
Dorchester Town Res
Parley Sports
3 - 0
1990/91
Dorchester Town Res
Flight Refuelling
Flight Refuelling
Dorchester Town Res
1 - 0
1989/90
Weymouth Res
Flight Refuelling
Hamworthy Utd
Wareham Rangers
2 - 2 *
1988/89
Shaftesbury
Westland Sports
Shaftesbury
Portland Utd
3 - 1 *
1987/88
Bridport
Flight Refuelling
Bridport
Shaftesbury
2 - 1 *
1986/87
Bridport
Parley Sports
Bridport
Parley Sports
1 - 0
1985/86
Bridport
Parley Sports
Parley Sports
Flight Refuelling
1 - 0
1984/85
Parley Sports
Poole Town Res
Sherborne Town
Portland Utd
5 - 1
1983/84
Parley Sports
Portland Utd
Westland Sports
Parley Sports
3 - 0
1982/83
Blandford Utd
Parley Sports
Flight Refuelling
Sherborne Town
2 - 1
1981/82
Sherborne Town
Parley Sports
Sherborne Town
Flight Refuelling
4 - 0
1980/81
Dorchester Town Res
Holt Utd
Sturminster Newton
Wareham Rangers
2 - 1
1979/80
Parley Sports
Blandford Utd
Flight Refuelling
Parley Sports
3 - 1
1978/79
Poole Town Res
Gillingham Town
Blandford Utd
Parley Sports
3 - 1
1977/78
Flight Refuelling
Parley Sports
Blandford Utd
Hamworthy Utd
2 - 2 *
1976/77
Hamworthy Utd
Parley Sports
Parley Sports
Gillingham Town
4 - 1
1975/76
Parley Sports
Hamworthy Utd
Blandford Utd
Parley Sports
1 - 0
1974/75
Blandford Utd
Parley Sports
Parley Sports
Dorchester Town Res
3- 1
1973/74
Parley Sports
Dorchester Town res
Blandford Utd
Parley Sports
2 - 0
1972/73
Parley Sports
Portland Utd
Bournemouth Water Co.
Parley Sports
1 - 1 *
1971/72
Parley Sports
Portland Utd
Parley Sports
Longfleet St Mary
2 - 0
1970/71
Portland Utd
Bournemouth Water Co.
Parley Sports
Dorchester Town Res
2 - 0
1969/70
Blandford Utd
Parley Sports
Parley Sports
Portland Utd Res
6 - 1
1968/69
Weymouth Res
Bournemouth Water Co.
Weymouth Res
Parley Sports
1 - 0
1967/68
Weymouth Res
Parley Sports
Parley Sports
Weymouth Res
4 - 1
1966/67
Parley Sports
Hamworthy
Parley Sports
Portland Utd Res
4 - 1
1965/66
Parley Sports
Yeovil Town Res
Yeovil Town Res
Vickers
4 - 1
1964/65
Parley Sports
Longfleet St Mary
Parley Sports
Wareham Rangers
3 - 1
1963/64
Parley Sports
Longfleet St Mary
Parley Sports
Wareham Rangers
2 - 2 *
1962/63
Parley Sports
Swanage Town
Parley Sports
Bridport
4 - 0
1961/62
Swanage Town
Hamworthy
Wareham Rangers
Portland Utd Res
4 - 3
1960/61
Swanage Town
Bridport
Dorchester Town res
Bridport
03-Jan
1959/60
Swanage Town
Bridport
Hamworthy
Swanage
4 - 0
1958/59
15th R.A.S.C.
Swanage Town
Bridport &
15th R.A.S.C
3 - 3 *�#
1957/58
Swanage Town
15th R.A.S.C.
Bridport &
15th R.A.S.C
2 - 2 *�#