2008/09 Chirnside
2007/08 Pencaitland
2006/07 Leithen Rovers
2005/06 Pencaitland
2004/05 Hawick Waverley
2003/04 Gala Rovers
2002/03 Earlston Rhymers
2001/02 Gala Rovers
2000/01 Gala Rovers
1999/00 Gala Rovers
1998/99 Duns Legion
1997/98 Duns Legion
1996/97 Chirnside
1995/96 Gala Rovers
1994/95 Chirnside
1993/94 Hawick Waverley
1992/93 Chirnside
1991/92 Hawick Legion
1990/91 Duns Legion
1989/90 Duns Legion
1988/89 Spittal Rovers
1987/88 Eyemouth Legion
1986/87 Gala Rovers
1985/86 Hawick Utd
1984/85 Hawick Utd
1983/84 Eyemouth Legion
1982/83 Hawick Utd
1981/82 Hawick Utd
1980/81 Gala Hotspur
1979/80 Gala Hotspur
1978/79 Gala Hotspur
1977/78 Gala Rovers**
1976/77 Leithen Rovers
1975/76 Hawick British Legion
1974/75 Greenlaw**
1973/74 Hawick Utd
1972/73 Gala Hotspur
1971/72 Hawick Utd
1970/71 Kelso Utd**
1969/70 Hawick British Legion
1968/69 Hawick British Legion
1967/68 Duns Ams
1966/67 Kelso Utd
1965/66 Hawick British Legion
1964/65 Hawick British Legion
1963/64 Gala Rovers
1962/63 Hawick British Legion
1961/62 Morebattle
1960/61 Morebattle
1959/60 Leithen Rovers**
1958/59 Leithen Rovers
1957/58 Greenlaw
1956/57 Greenlaw
1955/56 Greenlaw
1954/55 Gala Rovers
1953/54 Gala Rovers
1952/53 Gala Rovers
1951/52 Stow
1950/51 Gala Rovers
1949/50 Gala Rovers
1948/49 Hawick Royal Albert
1947/48 Hawick Sports Club L.N.E.R.
1938/39 Greenlaw
1937/38 Kelso Utd
1936/37 Peebles YMCA 2nd XI
** No entry on shield, details taken from the book 'From Mossilee to San Siro-The History of Gala Rovers' by Cubbs Turnbull
