In 1959, the Prince of Wales Stakes became the marquis event on the Fort Erie racing calendar. That was also the year the race became the second jewel in Canada's Triple Crown of Racing.

The first edition of the Prince of Wales Stakes was held at Thorncliffe Park in Toronto on June 3, 1929. During the 1930's, the race was restricted to 3-year olds foaled in Canada, utilizing the same format as both the Queen's Plate and the Breeders' Stakes, the other two legs of the Canadian Triple Crown
Over the years the purse structure has soared to over $500,000.00 from its initial running in 1929, which was worth $7,500. Until 1953, the race was known as the Prince of Wales Plate, but the size of the purse was dramatically less. After the first two runnings, the purse for the Prince of Wales was dropped to just $2,500 added as the country was in the midst of a depression.

In one year, 1949, there was no betting on the race. That year the field of five featured a powerful two-horse entry of Victory Arch and Filsis, two top-notch fillies. As everyone expected, they ran first and second with Victory Arch winning a thriller by a neck.

1959
1960
1961
1962
1963
1964
1965
1966
1967
1968
1969
1970
1971
1972
1973
1974
1975
1976
1977
1978
1979
1980
1981
1982
1983

New Providence
Bulpamiru
Song of Evan
King Gorm
Canebora
Canadillis
Good Old Mort
He's A Smoothie
Battling
Rouletabille
Sharp-Eyed Quillo
Almoner
New Pro Escar
Presidial
Tara Road
Rushton's Corsair
L'Enjoleur
Norcliffe
Dance in Time
Overskate
Mass Rally
Allan Blue
Cadet Corps
Runaway Groom
Archdeacon

 1984
1985
1986
1987
1988
1989
1990
1991
1992
1993
1994
1995
1996
1997
1998
1999
2000
2001
2002
2003
2004
2005
2006
2007

Val Dansant
Imperial Choice
Golden Choice
Coryphee
Regal Classic
With Approval
Izvestia
Dance Smartly
Ben Burb
Peteski
Bruce's Mill
Kiridashi
Stephanotis
Cryptocloser
Archers Bay
Gandria
Scatter the Gold
Win City
Le Cinquieme Essai
Wando
Bit O'Gold
Ablo
Shillelagh Slew
Alezzandro

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