"*" deceased
Gold Medal
| 1987 | * | M. Ex. Comp. Don Rennie | Saskatoon No. 4 | Saskatoon |
Silver Medal
| 2003 | * | M. Ex. Comp. James Hall | Assiniobia No. 15 | Assiniboia |
| 1987 | * | M. Ex. Comp. Bruce Saunders | Golden Compass No. 6 | Wolseley |
Bronze Medal
| 2024 | V. Ex. Comp. Mark Barclay | Battleford No. 9 | North Battleford | |
| 2023 | Rt. Ex. Comp. Alan Goode | Prince of Wales No. 27 | Regina | |
| 2022 | Rt. Ex. Comp. Mark Millar | Eagle Lake No. 20 | Kindersley | |
| 2020 | Rt. Ex. Comp. Richard Gutfriend | Prince of Wales No. 27 | Regina | |
| 2019 | Rt. Ex. Comp. Laughlin Arthur | Estevan No. 8 | Redvers | |
| 2018 | Rt. Ex. Comp. Robert Turczyn | Saskatoon No. 4 | Saskatoon | |
| 2017 | V. Ex. Comp. Dean Whitaker | Prince of Wales No. 27 | Regina | |
| 2016 | Rt. Ex. Comp. Donald A. Finan | Battleford No. 9 | North Battleford | |
| 2015 | Rt. Ex. Comp. John Bradley | Saskatoon No. 4 | Saskatoon | |
| 2014 | * | Rt. Ex. Comp. Lou Lintick | Prince Albert No. 2 | Prince Albert |
| 2013 | Rt. Ex. Comp. Fred Walker | Battleford No. 9 | North Battleford | |
| 2012 | Rt. Ex. Comp. Dan Gerle | Eagle Lake No. 20 | Kindersley | |
| 2011 | Rt. Ex. Comp. Lloyd Ramsdell | Prince of Wales No. 27 | Regina | |
| 2010 | * | Comp. Leroy Layman | Unity No. 10 | Swift Current |
| 2009 | * | V. Ex. Comp. John Anderson | Harlesden No. 33 | Saskatoon |
| 2008 | * | Rt. Ex. Comp. Harold Ball | Prince of Wales No. 27 | Regina |
| 2007 | * | Comp. John Weir | Unity No. 10 | Swift Current |
| 2006 | Ex. Comp. Walter R. Hudyma | Victoria No. 18 | Wynyard | |
| 2005 | V. Ex. Comp. Robert Decker | Prince of Wales No. 27 | Regina | |
| 2004 | Rt. Ex. Comp. Daniel McKay | Prince of Wales No. 27 | Regina | |
| 2003 | * | Rt. Ex. Comp. Fred Peterson | Cypress No. 26 | Maple Creek |
| 2002 | Comp. Tom Moore | Sheba No. 23 | Kamsack | |
| 2001 | * | Comp. Jim Wilkins | Saskatoon No. 4 | Saskatoon |
| 2000 | * | Comp. Alexander Robinson | Moose Jaw No. 3 | Moose Jaw |
| 1999 | * | V. Ex. Comp. Al Tingle | Prince of Wales No. 27 | Regina |
| 1998 | * | V. Ex. Comp. Clayton W. Brown | Golden Compass No. 6 | Wolseley |
| 1997 | * | Rt. Ex. Comp. Eric O. Burt | Harlesden No. 33 | Saskatoon |
| 1996 | * | V. Ex. Comp. Peter R. Teichroeb | Unity No. 10 | Swift Current |
| 1995 | * | Rt. Ex. Comp Hector S. Brown | Victoria No. 18 | Wynyard |
| 1994 | * | Rt. Ex. Comp. Lawrence Binkley | Cypress No. 16 | Maple Creek |
| 1993 | * | V. Ex. Comp. Cecil T. Hayward | Assiniboia No. 15 | Assiniboia |
| 1992 | * | V. Ex. Comp. Wilbur Randall | Prince of Wales No. 27 | Regina |
| 1991 | * | V. Ex. Comp. John Holmes | Eagle Lake # 20 | Kindersley |
| 1990 | * | V. Ex. Comp. Gordon L. Brown | King George No. 14 | Yorkton |
| 1989 | * | V. Ex. Comp. James G. Martin | Prince of Wales No. 27 | Regina |
| 1988 | * | V. Ex. Comp. William G. Cable | Estevan No. 8 | Estevan |
| 1987 | * | Rt. Ex. Comp. John S. Sangster | Orient No. 13 | Moosomin |
| 1986 | * | V. Ex. Comp. Carl L. Riley | Assiniboia No. 15 | Assiniboia |
| 1985 | * | Rt. Ex. Comp. Ben Morrison | Harlesden No. 33 | Saskatoon |
| 1984 | * | V. Ex. Comp. J. Preston Andrews | Weyburn No. 7 | Weyburn |
| 1983 | * | Rt. Ex. Comp. Edwin E. Longmire | Eagle Lake No. 20 | Kindersley |
| 1982 | * | Rt. Ex. Comp. John J. Bole | Victoria No. 18 | Wynyard |
| 1981 | * | Rt. Ex. Cop. Albert Smith | Saskatoon No. 4 | Saskatoon |
| 1980 | * | Rt. Ex. Comp. John G. Walker | Battleford No. 9 | Battleford |
| 1979 | * | V. Ex. Comp. Alexander Grant | Unity No. 10 | Swift Current |
| 1978 | * | Rt. Ex. Comp. W.G. White | Victoria No. 18 | Wynyard |
| 1977 | * | V. Ex. Comp. W. L. Sharpe | Weyburn No. 7 | Weyburn |
| 1976 | * | Ex. Comp. H.S. Stevens | Shaunavon No. 17 | Shaunavon |
| 1975 | * | V. Ex. Comp. Stanley T. Dunn | Saskatoon No. 4 | Saskatoon |
| 1974 | * | Comp. Harry Bell | Prince of Wales No. 27 | Regina |
| 1973 | * | V. Ex. Comp. E. W. Morgan | Eagle Lake No. 20 | Kindersley |
| 1972 | * | Comp. Charles Holman | Moose Jaw # 3 | Moose Jaw |
| 1971 | * | Rt. Ex. Comp. O. Alfred Olson | Sheba No. 23 | Kamsack |
| 1970 | * | Rt. Ex. Comp. Irwin Scott | Melfort No. 22 | Tisdale |
| 1969 | * | V. Ex. Comp. F.T. Cameron | Victoria No. 18 | Wynyard |
| 1968 | * | V. Ex. Comp. Earl Meahan | Victory No. 28 | Elrose |
| 1967 | * | Rt. Ex. Comp. J.T. Tomlinson | Prince Albert No. 2 | Prince Albert |
| 1966 | * | Ex. Comp. Arthur Goodwin | Golden Compass No. 6 | Wolseley |
| 1965 | * | Comp. M. Sheridan | Saskatoon No. 4 | Saskatoon |
| 1964 | * | Comp. Charles A. Morton | Wascana No. 1 | Regina |
| 1963 | * | Comp. Harold Lumb | Assiniboia No. 15 | Assiniboia |
| 1962 | * | Comp. T.W. Gilmour | Etomami No. 30 | Hudson Bay |
| 1961 | * | Ex. Comp. Frederick Horsey | Shaunavon No. 17 | Shaunavon |
| 1960 | * | Ex. Comp. Edwin L. Fowler | Victoria No. 18 | Wynyard |
| 1959 | * | V. Ex. Comp. William Kelly | Moose Jaw No. 3 | Moose Jaw |
| 1958 | * | V. Ex. Comp. John Gaffield | Acacia No. 24 | Cabri |
| 1957 | * | Rt. Ex. Comp. Harry Mitchell | Weyburn No. 7 | Weyburn |
| 1956 | * | Comp. Arthur Webb | Saskatoon No. 4 | Saskatoon |
| 1955 | * | V. Ex. Comp. Thomas Saunders | King George No.14 | Yorkton |
| 1954 | * | Rt. Ex. Comp. William Fell | Melfort No. 22 | Tisdale |
| 1953 | * | Rt. Ex. Comp. John F. Frook | Cypress No. 26 | Gull Lake |
| 1952 | * | V. Ex. Comp. C. Chas. Graham | Wascana No. 1 | Regina |