Year
Winner
Runner-up
1887/88
Milford
1888/89
Milford
Loughgall
1889/90
1st Lancashire Regiment
1890/91
Donacloney
Milford
1891/92
Banford
Brownlow
1892/93
Donacloney
Portadown
1893/94
Royal Irish Rifles
1894/95
Cornwall Regiment
Glenavon
1895/96
Donacloney
Cookstown
1896/97
Milltown Wanderers
Portadown
1897/98
Glenavon
Portadown
1898/99
Portadown
Lurgan Star
1899/1900
Portadown
Cookstown
1900/01
Donacloney
1901/02
Glenavon
1902/03
Portadown
Glenavon
1902/03
Portadown
Glenavon
1903/04
Portadown
Monaghan
1904/05
Glenavon
Portadown
1905/06
Portadown
Glenavon
1906/07
Glenavon
Portadown
1907/08
Portadown
Glenavon
1908/09
Glenavon
Portadown
1909/10
Portadown
Lurgan Celtic
1910/11
Glenavon
1911/12
Lurgan Celtic
Portadown
1912/13
Lurgan Celtic
Bessbrook Strollers
1913/14
Lurgan Rangers
Glenavon Reserves
1914/15
Lurgan Celtic
Portadown
1915/16
Unknown
1916/17
Unknown
1917/18
Unknown
1918/19
Unknown
1919/20
Unknown
1920/21
Unknown
1921/22
Unknown
1922/23
Unknown
1923/24
Unknown
1924/25
Glenavon
Lurgan 'B' Specials
1925/26
Glenavon
Portadown
1926/27
Banbridge Town- Cup & Medals withheld after Protest by Newry Town
1927/28
Unknown
1928/29
Unknown
1929/30
Unknown
1930/31
Glenavon
Sunnyside
1931/32
Portadown
1932/33
Glenavon
1933/34
Portadown
1934/35
Gilford Crusaders
Portadown
1935/36
Sunnyside
1936/37
Newry Town
1937/38
Glenavon
Newry Town
1938/39
Hanover United FC
1946/47
Portadown Reserves
Sunnyside
1947/48
Glenavon Reserves
1948/49
Banbridge Town
Gilford Crusaders
1949/50
Banbridge Town
Dromore Athletic
1950/51
Seapatrick
1951/52
Seapatrick
Bessbrook
1952/53
Tandragee Rovers
1953/54
Tandragee Rovers
Seapatrick
1954/55
Seapatrick
Bessbrook
1955/56
Tandragee Rovers
Bessbrook
1956/57
Newry Town
Tandragee Rovers
1957/58
Glenavon Reserves
Newry Town
1958/59
Banbridge Town
1959/60
Tandragee Rovers
Woodville Rec
1960/61
Portadown Reserves
Banbridge Town
1961/62
Tandragee Rovers
Glenavon Reserves
1962/63
Portadown Reserves
1963/64
Newry Town
Portadown Reserves
1964/65
Portadown Reserves
Banbridge Town
1965/66
Glenavon Reserves
1966/67
Newry Town
Tandragee Rovers
1967/68
Blane's
Tandragee Rovers
1968/69
Newry Town
Damolly
1969/70
Portadown Reserves
Tandragee Rovers
1970/71
Dungannon Swifts
1971/72
Glenavon Reserves
1972/73
New Century
1973/74
Banbridge Town
1974/75
Newry Town
1975/76
Dungannon Swifts
1976/77
Glenavon Reserves
1977/78
Newry Town
1978/79
Newry Town
1979/80
Banbridge Town
1980/81
Portadown
1981/82
Portadown
1982/83
Portadown
1983/84
Glenavon
1984/85
Newry Town
1985/86
Glenavon
1986/87
Newry Town
1987/88
Dungannon Swifts
1988/89
Glenavon
1989/90
Newry Town
1990/91
Glenavon
1991/92
Glenavon - Trophy withheld as Glenavon fielded ineligible player
Portadown
1992/93
Portadown
1993/94
Portadown
1994/95
Portadown
1995/96
Bangor
1996/97
Dungannon Swifts
1997/98
Portadown
Dungannon Swifts
1998/99
Glenavon
1999/2000
Newry Town
2000/01
Armagh City
2001/02
Portadown
Lurgan Celtic
2002/03
Portadown
2003/04
Loughgall
Newry Town
2004/05
Glenavon
2005/06
Dungannon Swifts
2006/07
Newry City
2007/08
Loughgall
2008/09
Dungannon Swifts
2009/10
Glenavon
2010/11
Glenavon
2011/12
Newry City
2012/13
Dungannon Swifts
Banbridge Town
2013/14
Dungannon Swifts
Annagh Utd
2014/15
Dungannon Swifts
Armagh City
2015/16
Dungannon Swifts
Armagh City
2016/17
Warrenpoint Town
Armagh City
2017/18
Glenavon
Newry City AFC
2018/19
Glenavon
2019/20
Loughgall
Glenavon