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 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.

Records Speed record: 1:20.54 - Verne's Baby (2006) - 7 furlongs on dirt

Most wins: 2 - Krz Ruckus (2001, 2002)

Most wins by a jockey: 3 - Eurico Rosa da Silva (2014, 2016, 2017) 3 - Justin Stein (2011, 2012, 2013)

Most wins by a trainer: 3 - Robert Tiller (2007, 2015, 2017)

Most wins by an owner: 2 - Buttigieg Training Centre (2011, 2013, 2018) 2 - Ron Guidolin et al. (2001, 2002) 2 - Bruno Schickendanz (2009, 2016)

Winners of the Overskate Stakes Year Winner Age Jockey Trainer Owner Time Ref2020Not So Quiet5Rafael HernandezMark CasseHeste Sport1:31.032019Dixie's Gamble4Luis ContrerasJosie CarrollIvan Dalos1:25.032018Thor's Rocket5Alan GarciaPaul ButtigiegButtigieg training centre and Gus Viahos1:22.482017Pink Lloyd5E. Rosa Da SilvaRobert TillerEntourage Stable1:21.732016Touch of DisneyO. MorenoN. McKnightBruno Schickendanz1:21.512015GoodoldhockeygameE. Rosa Da SilvaRobert TillerFrank Di Giulio Jr.1:22.722014Paso DobleE. Rosa Da SilvaM. FournierCentennial Farms1:21.432013Phil's DreamJustin SteinP. ButtigiegButtigieg Training Centre1:21.312012Bear's PeakJ. SteinR. BakerBear Stables1:22.462011Gypsy RingJ. SteinP. ButtigiegPaul Buttigieg1:21.542010Sand CoveJ. JonesRoger AttfieldRalph Johnson1:22.332009Yummy With Butter5Tyler PizarroMark FournierBruno Schickedanz1:22.152008Not Bourbon3Jono JonesRoger AttfieldCharles E. Fipke1:21.782007Dancer's Bajan3Corey FraserRobert P. Tiller3 Sons Racing Stable1:23.212006Verne's Baby4Emile RamsammySid C. AttardG B Stable1:20.542005Mister Coop6Emile RamsammyDaniel J. VellaR.M.C. Stable 1:21.302004Barath5Harry VegaGuadalupe PreciadoTze On Yeung1:23.062003Mulligan The Great4James McKnightCliff C. HopmansCharles E. Simmons1:22.022002Krz Ruckus5Dino Luciani Mike P. DePauloRon Guidolin et al.1:23.562001Krz Ruckus4Dino Luciani Mike P. DePaulo Ron Guidolin et al.1:24.272000One Way Love5Patrick HusbandsAbraham R. KatryanB. Schickedanz & J. Hillier1:22.371999Randy Regent5Todd KabelMark FrostadSam-Son Farms1:22.401998Deputy Inxs7Na Somsanith Audre Cappuccitti Audre & Gordon Cappuccitti1:23.201997Seismic Report6Mickey WallsJoe WallsShelter Valley Farm1:22.80

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