The Sky Classic Stakes is a Canadian Grade II Thoroughbred horse race run annually at Woodbine Racetrack in Toronto, Ontario. Raced in mid to late September on turf over a distance of 1-1/4 miles (10 furlongs), it is open to horses three years of age and older. In recent years it has become a major prep race for local horses looking to go on to run against the best horses from around the world in Woodbine's $2 million Canadian International.

Renamed in 1995 to honor Canadian Horse Racing Hall of Fame inductee, Sky Classic, the race was first run at the Old Woodbine Racetrack in 1902 as the Jockey Club Cup Handicap. It was raced on dirt from inception until 1956 but became a turf race the following year when moved to the new Woodbine racing facility. Over the years, it has been run at various distances.