|
| 1951-52 Eyemouth Swifts AFC |
| 1952-53 Peebles Y.M.C.A. |
| 1953-54 Gala Rovers AFC |
| 1954-55 Greenlaw AFC |
| 1955-56 Greenlaw AFC |
| 1956-57 Gordon Westruther AFC |
| 1957-58 Broughton United AFC |
| 1958-59 Selkirk Thistle AFC |
| 1959-60 Gordon Westruther AFC |
| 1960-61 Tweeddale Rovers AFC |
| 1961-62 Morebattle AFC |
| 1962-63 Gala Rovers AFC |
| 1963-64 Gala Rovers AFC |
| 1964-65 Gala AFC |
| 1965-66 Tweeddale Rovers AFC |
| 1966-67 Tweeddale Rovers AFC |
| 1967-68 Tweeddale Rovers AFC |
| 1968-69 Symington AFC |
| 1969-70 Lauder AFC |
| 1970-71 Symington AFC |
| 1971-72 Hawick United AFC |
| 1972-73 Kelso United AFC |
| 1973-74 Tweeddale Rovers AFC |
| 1974-75 Tweeddale Rovers AFC |
| 1975-76 Tweeddale Rovers AFC |
| 1976-77 Dunbar Blue Circle AFC |
| 1977-78 Dunbar Blue Circle AFC |
| 1978-79 Lanark Thistle AFC |
| 1979-80 Lanark Thistle AFC |
| 1980-81 Shotts M.D.AFC |
| 1981-82 Monteith AFC |
| 1982-83 Monteith AFC |
| 1983-84 Tweedale Rovers AFC |
| 1984-85 Douglas Thistle AFC |
| 1985-86 Monteith AFC |
| 1986-87 Hawick Legion AFC |
| 1987-88 Maxwelltown H.S.F.P.AFC |
| 1988-89 Chirnside AFC |
| 1989-90 Rigside AFC |
| 1990-91 Monteith AFC |
| 1991-92 Duns Legion AFC |
| 1992-93 Shotts Y.M.C.A. A.F |
| 1993-94 Monteith AFC |
| 1994-95 Shotts Y.M.C.A. AFC |
| 1995-96 Kirk United AFC |
| 1996-97 Duns Legion AFC |
| 1997-98 Duns Legion AFC |
| 1998-99 Upper Annandale AFC |
| 1999-00 Coldstream AFC |
| 2000-01 Symington Tinto AFC |
| 2001-02 Kirkconnell AFC |
| 2002-03 Symington Tinto AFC |
| 2003-04 Monteith AFC |
| 2004-05 Chirnside AFC |
| 2005-06 Hawick Waverley AFC |
| 2006-07 Leithen Rovers AFC |
| 2007-08 Gala Rovers AFC |
| 2008-09 Chirnside AFC |
| 2009-10 Newtongrange Star “A” AFC |
| 2010-11 Leithen Rovers AFC |
| 2011-12 Leithen Rovers AFC |
| 2012-13 Pencaitland AFC |
| 2013-14 Leithen Rovers AFC |
| 2014-15 Shotts Victoria AFC |
| 2015-16 Danderhall Miners AFC |
| 2016-17 Danderhall Miners AFC |
| 2017-18 Hawick Waverley AFC |
| 2018-19 Carluke Hearts AFC |
