The Grey Stakes is a Canadian Thoroughbred horse race held annually during the first week of October at Woodbine Racetrack in Toronto. A Grade III, it is open to two-year-old horses and is raced on dirt at a distance of 1+1⁄16 miles. Since 2006, the dirt racing surface at Woodbine Racetrack has been the synthetic Polytrack.

Inaugurated as the Grey Stakes at the Old Woodbine Racetrack in 1906, it was named in honor of the then Governor General of Canada, Earl Grey. Over the years it has been run at various distances:

• 1 mile : 1906-1929 (Old Woodbine Racetrack)
• 1 mile 70 yards : 1930-1955 (Old Woodbine Racetrack)
• 1+1⁄16 miles : 1956 to present at Woodbine Racetrack

J. K. L. Ross, owner of the first United States Triple Crown Champion, Sir Barton, won this race five years in a row with future U.S. Racing Hall of Fame trainer, Henry McDaniel. In 1926 Henry McDaniel added another win, making him the leader among all winning trainers.

Notable horses who have won the race includes future Canadian Horse Racing Hall of Fame inductees Horometer (1933), Kennedy Road (1970), Sunny's Halo (1982), and Sky Classic (1989). Dancer's Image won the 1967 race and went on to capture the following year's Kentucky Derby, as did Mine That Bird in 2009. Since the creation of the Breeder's Cup races in 1984, Macho Uno is the only horse to have won the Grey Stakes then gone on to win that year's Breeders' Cup Juvenile.

Famous horses who did not win the Grey Stakes include Display who ran second in 1925 but was the ensuing year's Preakness Stakes winner. As well, the 1997 Belmont Stakes winner Touch Gold finished third in the 1996 running of the Grey Stakes.

Time record: (at current 1+1⁄16 miles distance)

• 1:43.20 - Black Cash (1997)

Most wins by an owner:

• 5 - J. K. L. Ross (1921, 1922, 1923, 1924, 1925)
• 5 - Sam-Son Farm (1984, 1986, 1987, 1989, 2004)

Most wins by a jockey:

• 5 - Pat Remillard (1937, 1943, 1947, 1961, 1963)
• 5 - Dave Penna (1982, 1986, 1987, 1992, 1995)

Most wins by a trainer:

• 6 - Henry McDaniel (1921, 1922, 1923, 1924, 1925, 1926)

• Road to the Kentucky Derby
• List of Canadian flat horse races