Sir Hugh S. Roberton donated the Sir Hugh Roberton Trophy to the Winnipeg Music Festival in 1939. This trophy was originally awarded annually for the most outstanding performance by a School Chorus, Grade 1 to Grade 6. Today, school choruses Kindergarten to Grade 6 are eligible.
Born in 1874, Sir Hugh Roberton became prominent in the British Isles as a composer and director and was well known throughout the musical world as director of the famous Glasgow Orpheus Choir. He was knighted in 1931. He was a popular adjudicator in the Winnipeg Music Festival.
| Year | Winner | Year | Winner | Year | Winner |
| 1939
|
Aberdeen School
|
1964
|
Angus McKay School
|
1989
|
Donwood School
|
| 1940
|
Aberdeen School
|
1965
|
Neil Campbell School
|
1990
|
John de Graff School
|
| 1941
|
Aberdeen School
|
1966
|
Lord Wolseley School
|
1991
|
Donwood School
|
| 1942
|
Somerset School
|
1967
|
Robert H. Smith School
|
1992
|
John de Graff School
|
| 1943
|
Glenwood School
|
1968
|
Angus McKay School
|
1993
|
John de Graff School
|
| 1944
|
William Whyte School
|
1969
|
Angus McKay School
|
1994
|
Dieppe School
|
| 1945
|
William Whyte School
|
1970
|
Brock-Corydon School
|
1995
|
Tyndall Park School
|
| 1946
|
David Livingstone School
|
1971
|
Robert H. Smith
|
1996
|
Ralph Brown School
|
| 1947
|
Greenway School
|
1972
|
Ralph Brown School
|
1997
|
Garden Grove School
|
| 1948
|
Prince Edward School
|
1973
|
Grosvenor School
|
1998
|
Tyndall Park School
|
| 1949
|
John M. King School
|
1974
|
Neil Campbell School
|
1999
|
Balmoral Hall
|
| 1950
|
King Edward School
|
1975
|
William Osler School
|
2000
|
Balmoral Hall Grades 3-4
|
| 1951
|
Greenway School
|
1976
|
Lord Roberts & Dr. F. W. L.
Hamilton
|
2001
|
École Robert H. Smith School
|
| 1952
|
John M. King School
|
1977
|
Maple Leaf School
|
2002
|
Balmoral Hall Grades 1-3
|
| 1953
|
Lord Wolseley School
|
1978
|
Maple Leaf School
|
2003
|
Maple Leaf School
|
| 1954
|
Lord Wolseley School
|
1979
|
Angus McKay School
|
2004
|
Balmoral Hall School
|
| 1955
|
Lord Wolseley School
|
1980
|
Dr. F. W. L. Hamilton
|
2005
|
Balmoral Hall School
|
| 1956
|
Lord Wolseley School
|
1981
|
Maple Leaf School
|
2006 | École Dieppe Choir |
| 1957
|
Lord Wolseley School
|
1982
|
Balmoral Hall
|
2007 | École Dieppe Choir |
| 1958
|
Munroe School
|
1983
|
John de Graff School
|
2008 | École Dieppe Grades 1-3 Choir |
| 1959
|
Harrow School
|
1984
|
Donwood Elementary School
|
2009 | Linden Christian School |
| 1960
|
Lord Wolseley School
|
1985
|
John de Graff School
|
2010 | Bairdmore Balladeers |
| 1961
|
Robert H. Smith School
|
1986
|
Donwood School Boys' Choir
|
2011 | École Garden Grove School Primary Choir |
| 1962
|
Brock-Corydon School
|
1987
|
Donwood School
|
||
| 1963
|
Riverview School
|
1988
|
no entry
|
||