The Classy 'N Smart Stakes is a Thoroughbred horse race run annually in mid October at Woodbine Racetrack in Toronto, Ontario, Canada. An Ontario Sire Stakes, it is a restricted race for fillies and mares, age three and older. It is contested over a distance of one and one-sixteenth miles (8.5 furlongs) on Polytrack synthetic dirt and currently carries a purse of $94,913.
Inaugurated in 1997, the race was named to honor Sam-Son Farm's Champion filly and Canadian Horse Racing Hall of Fame inductee, Classy 'n Smart.
Records Speed record: 1:42.53 – Strut the Course (2014)
Most wins: 3 – Brass in Pocket (2002, 2003, 2004)
Most wins by an owner: 3 – Frank Di Giulio, Jr. (2002, 2003, 2004)
Most wins by a jockey: 3 – Todd Kabel (2001, 2002, 2004)
Most wins by a trainer: 4 – Robert P. Tiller (2002, 2003, 2004, 2016)
Winners Year Winner Age Jockey Trainer Owner Time2016Sweater Weather5Jermaine V. BridgmohanRobert P. TillerFrank D. Di Giulio, Jr.1:45.112015Flipcup4Alan GarciaWilliam I. MottTeam Penney/Wachtel Stable/Brous Stable 1:44.382014Strut the Course4Eurico Rosa da SilvaBarb MinshallJohn Unger1:42.532013Moonlit Beauty7David MoranJohn LeBlanc, Jr.William Gierkink1:45.132012Moonlit Beauty6Eurico Rosa Da SilvaJohn LeBlanc, Jr.William Gierkink1:43.542011Bear It's Time3Emma-Jayne WilsonReade BakerBear Stables1:44.282010Impossible Time5Jono JonesRoger AttfieldCharles E. Fipke1:43.782009You Will Love Me 5Chantal SutherlandRobert BarnettWilliam Jones 1:45.522008Bold Corky4Tyler PizarroWillie ArmataRainbow St/All Day Racing St1:44.572007Financingavailable6James McAleneyLorne RichardsK. K. Sangara1:45.782006Financingavailable5James McAleneyLorne RichardsK. K. Sangara1:44.572005Schooner Bay4Emile RamsammyDavid R. BellMelnyk Racing Stables1:46.032004Brass in Pocket5Todd KabelRobert P. TillerFrank Di Giulio, Jr.1:46.022003Brass in Pocket4David ClarkRobert P. TillerFrank Di Giulio, Jr.1:45.982002Brass in Pocket3 Todd KabelRobert P. TillerFrank Di Giulio, Jr.1:43.212001Moonlight Affair3Todd KabelTino AttardStronach Stables1:45.192000Katherine of Ascot4Constant MontpellierReade BakerTerra Farm1:45.911999Princess Alicia3Patrick HusbandsSid C. AttardGoldmart Farms 1:45.151998No Foul Play4Steve BahenMargaret A. SpencerMargaret A. Spencer1:44.801997Blue and Red5Rui PimentelSid C. AttardJim Dandy Stable1:42.60
References The Classy 'N Smart Stakes at Pedigree Query The 2008 Classy 'N Smart Stakes at Woodbine Entertainment