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The Overskate Stakes is a Canadian Thoroughbred horse race run annually during the latter part of October at Woodbine Racetrack in Toronto, Ontario. An Ontario Sire Stakes, it is a restricted race for horses age three and older. It is currently contested over a distance of 7+1⁄2 furlongs on Woodbine's inner turf course with a purse of C$100,000. Inaugurated in 1997, it is named in honor of Overskate, a Canadian Horse Racing Hall of Fame horse who holds the record for most Sovereign Award with nine. Prior to 2020, the race was run on the main track at a distance of 7 furlongs.