| YEAR | NAME | CLUB | YEAR | NAME | CLUB | YEAR | NAME | CLUB | ||
| 1884 | John Leys | RCYC | 1926 | T A E World | QCYC | 1968 | Theodore Booth | YYC | ||
| 1885 | John T Mott | OswYC | 1927 | T A E World | QCYC | 1969 | Ian Morch | BQYC | ||
| 1886 | W H Biggar | BQYC | 1928 | T A E World | QCYC | 1970 | Frank R Shumway | RYC | ||
| 1887 | J B Carruthers | KYC | 1929 | T A E World | QCYC | 1971 | Frank R Shumway | RYC | ||
| 1888 | George H Newell | RYC | 1930 | T A E World | QCYC | 1972 | George Couch | CresYC | ||
| 1889 | J F Monck | HYC | 1931 | T K Wade | RCYC | 1973 | George Couch | CresYC | ||
| 1890 | A R Boswell | RCYC | 1932 | E A Barnes | CresYC | 1974 | Bunting Crocker | RCYC | ||
| 1891 | John T Mott | OswYC | 1933 | E A Barnes | CresYC | 1975 | Bunting Crocker | RCYC | ||
| 1892 | Mat. Cartwright | RYC | 1934 | L F Grant | KYC | 1976 | Elmer J Doyle, Jr | YYC | ||
| 1893 | F S Malloch | RHYC | 1935 | L F Grant | KYC | 1977 | Elmer J Doyle, Jr | YYC | ||
| 1894 | A R Boswell | RCYC | 1936 | W F N Windeyer | RCYC | 1978 | David Heron | PCYC | ||
| 1895 | Aemilius Jarvis | RCYC | 1937 | W F N Windeyer | RCYC | 1979 | David Heron | PCYC | ||
| 1896 | Aemilius Jarvis | RCYC | 1938 | W F N Windeyer | RCYC | 1980 | William J Stolze | RYC | ||
| 1897 | E H Ambrose | RHYC | 1939 | Wilmot V Castle, Sr. | RYC | 1981 | William J Stolze | RYC | ||
| 1898 | Frank Strange | Kyc | 1940 | Robert Barr | RCYC | 1982 | Helen Ingerson | RYC | ||
| 1899 | A G Wright | RYC | 1941 | Robert Barr | RCYC | 1983 | Helen Ingerson | RYC | ||
| 1900 | J S Thompson | BQYC | 1942 | Robert Barr | RCYC | 1984 | Harvard B Kolm | YYC | ||
| 1901 | R A Lucas | RHYC | 1943 | Robert Barr | RCYC | 1985 | Harvard B Kolm | YYC | ||
| 1902 | F M Gray | RCYC | 1944 | Robert Barr | RCYC | 1986 | Henry W Williams | RYC | ||
| 1903 | Frank Strange | KYC | 1945 | William P Barrows | RYC | 1987 | Henry W Williams | RYC | ||
| 1904 | John T Mott | OswYC | 1946 | William P Barrows | RYC | 1988 | Robert Thompson | RHYC | ||
| 1905 | T B Pritchard | RYC | 1947 | Charles J Spaulding | YYC | 1989 | Robert Thompson | RHYC | ||
| 1906 | E Finch Noyes | RHYC | 1948 | Charles J Spaulding | YYC | 1990 | Robert Thompson | RHYC | ||
| 1907 | T A E World | QCYC | 1949 | Charles J Spaulding | YYC | 1991 | Edward L St.George | SBYC | ||
| 1908 | C G Marlatt | RCYC | 1950 | C W Gamble | CYC | 1992 | Edward L St.George | SBYC | ||
| 1909 | C G Marlatt | RCYC | 1951 | C W Gamble | CYC | 1993 | Matthew D Georger | BCC | ||
| 1910 | C G Marlatt | RCYC | 1952 | Eugene G Sorsoleil | RCYC | 1994 | Matthew D Georger | BCC | ||
| 1911 | Samuel Vila | RHYC | 1953 | Eugene G Sorsoleil | RCYC | 1995 | Janet Willings | NYC | ||
| 1912 | George W Reeves | CresYC | 1954 | Clifford Lunt | RHYC | 1996 | Janet Willings | NYC | ||
| 1913 | George W Reeves | CresYC | 1955 | P J Hunt | YYC | 1997 | H Robb Holt | RYC | ||
| 1914 | George W Reeves | CresYC | 1956 | P J Hunt | YYC | 1998 | H Robb Holt | RYC | ||
| 1915 | George W Reeves | CresYC | 1957 | A H Gorsline | SBYC | 1999 | A.H.Hooker | YYC | ||
| 1916 | George W Reeves | CresYC | 1958 | J R Mason | RCYC | 2000 | A.H.Hooker | YYC | ||
| 1917 | George W Reeves | CresYC | 1959 | J R Mason | RCYC | 2001 | C. Andrews | ABYC | ||
| 1918 | George W Reeves | CresYC | 1960 | Karl Smither | BCC | 2002 | Edward L. St. George | SBYC | ||
| 1919 | Samuel Vila | RHYC | 1961 | Karl Smither | BCC | 2003 | Michael J. Foley | SBYC | ||
| 1920 | N R Gooderham | RCYC | 1962 | Arn Gorman | QCYC | 2004 | Michael J. Foley | SBYC | ||
| 1921 | S Lansing | CresYC | 1963 | Arn Gorman | QCYC | 2005 | Ursula Cattelan | NYC | ||
| 1922 | W B Casey | KYC | 1964 | Newton Castle | RYC | 2006 | Ursula Cattelan | NYC | ||
| 1923 | W B Casey | KYC | 1965 | Newton Castle | RYC | 2007 | Patrick Lymburner | PCYC | ||
| 1924 | C H O Pook | RCYC | 1966 | Fred Brade | RHYC | 2008 | Patrick Lymburner | PCYC | ||
| 1925 | William P Barrows | RYC | 1967 | Theodore Booth | YYC | 2009 | Robert Elliot | GYC |