Year
Winner
Runner-up
1909/10
Glenavon Reserves
1910/11
Glenavon Reserves
1911/12
Bessbrook
1912/13
Bessbrook
1913/14
Lurgan Rangers
1914/15
No Competition
1915/16
No Competition
1916/17
Parkside (Lurgan)
1917/18
Glenavon Reserves
1918/19
Celtic Juniors
1919/20
Lurgan Rangers
1920/21
Greenview
1921/22
Armagh United
1922/23
Greenview
1923/24
Lurgan 'B' Specials
1924/25
Armagh United
1925/26
Armagh United
1926/27
Edenderry Arrows
1927/28
Portadown Reserves
1928/29
Portadown Reserves
1929/30
Lurgan Rangers
1930/31
Holm Factory
1931/32
Dungannon Town
1932/33
Lurgan Rangers Reserves
1933/34
Lurgan Distillery
1934/35
Newry United
1935/36
Portadown Crusaders
1936/37
Lurgan Rangers
Eden Villa
1937/38
Eden Villa
1938/39
Bessbrook Strollers
1939/40
Shankill YM
1940/41
Shankill YM
1941/42
No Competition
1942/43
Long Kesh
1943/44
Deramore
1944/45
NFS (Portadown)
1945/46
Sunnyside
1946/47
Holm Factory
1947/48
Holm Factory Reserves
1948/49
Gilford Crusaders
1949/50
Dungannon Swifts
1950/51
Shankill Villa
1951/52
Seapatrick Rec.
1952/53
Holm Factory
1953/54
Lurgan Boys
1954/55
Bessbrook Rangers
1955/56
Dungannon Swifts
1956/57
Queens Park
Laurelvale
1957/58
Bleary
1958/59
Woodville Rec.
1959/60
Newry Utd Youth
1960/61
Armagh BC
1961/62
Seapatrick
1962/63
Lurgan Institute
1963/64
Gilford
1964/65
Lurgan BC
1965/66
Queens Park Swifts
1966/67
Damolly
1967/68
Blanes
1968/69
Damolly
1969/70
Milford Everton
1970/71
Dungannon Swifts
1971/72
Lurgan Celtic
1972/73
Waringstown Utd
1973/74
Benburb
1974/75
Rathfriland
1975/76
Rathfriland
1976/77
Shield Withheld
1977/78
Rathfriland
1978/79
Armagh Thistle
1979/80
Portadown BBOB
1980/81
Shamrock Rovers (Newry)
1981/82
Shamrock Rovers (Newry)
1982/83
Oxford Utd
1983/84
Oxford Utd
1984/85
Lurgan Utd
1985/86
Guys
1986/87
Craigpark
1987/88
Camlough Rovers
1988/89
Seapatrick
1989/90
Oxford Utd
1990/91
Oxford Utd
1991/92
Oxford Utd
1992/93
Oxford Utd
1993/94
Dungannon Swifts
1994/95
Oxford Utd
1995/96
Newry Celtic
1996/97
Hill Street
1997/98
Hill Street
1998/99
St. Mary's
1999/2000
Riverdale
2000/01
Newry Celtic
2001/02
Hill Street
2002/03
Hill Street
2003/04
Hill Street
2004/05
Shanro Santos
2005/06
Bessbrook Utd
2006/07
Bessbrook Utd
2007/08
Windmill Stars
2008/09
Windmill Stars
2009/10
St. Mary's
2010/11
Celtic Club No.1
2011/12
Ambassadors
2012/13
Silverwood Utd
Armagh Rovers
2013/14
Windmill Stars
Orchard City
2014/15
Windmill Stars
Orchard City
2015/16
Ballyoran
Silverwood Utd
2016/17
Cleary Celtic
Cookstown Olympic
2017/18
Coalisland Athletic
Loughgall Res
2018/19
2019/20
Rathfriland Rangers Reserves
Coalisland Athletic
2020/21