Classy 'N Smart Stakes
| Class | Restricted Stakes | 
|---|---|
| Location | Woodbine Racetrack Toronto, Ontario, Canada | 
| Inaugurated | 1997 | 
| Race type | Thoroughbred - Flat racing | 
| Website | web | 
| Race information | |
| Distance | 1+1⁄16 miles (8.5 furlongs) | 
| Surface | Polytrack synthetic dirt | 
| Track | left-handed | 
| Qualification | Three-year-olds and up | 
| Weight | Assigned | 
| Purse | $94,913 (2016) | 
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: (Through 1998, Woodbine times were recorded in fifths of a second. Since 1999 they are in hundredths of a second)
- 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 | Time | 
|---|---|---|---|---|---|---|
| 2016 | Sweater Weather | 5 | Jermaine V. Bridgmohan | Robert P. Tiller | Frank D. Di Giulio, Jr. | 1:45.11 | 
| 2015 | Flipcup | 4 | Alan Garcia | William I. Mott | Team Penney/Wachtel Stable/Brous Stable | 1:44.38 | 
| 2014 | Strut the Course | 4 | Eurico Rosa da Silva | Barb Minshall | John Unger | 1:42.53 | 
| 2013 | Moonlit Beauty | 7 | David Moran | John LeBlanc, Jr. | William Gierkink | 1:45.13 | 
| 2012 | Moonlit Beauty | 6 | Eurico Rosa Da Silva | John LeBlanc, Jr. | William Gierkink | 1:43.54 | 
| 2011 | Bear It's Time | 3 | Emma-Jayne Wilson | Reade Baker | Bear Stables | 1:44.28 | 
| 2010 | Impossible Time | 5 | Jono Jones | Roger Attfield | Charles E. Fipke | 1:43.78 | 
| 2009 | You Will Love Me | 5 | Chantal Sutherland | Robert Barnett | William Jones | 1:45.52 | 
| 2008 | Bold Corky | 4 | Tyler Pizarro | Willie Armata | Rainbow St/All Day Racing St | 1:44.57 | 
| 2007 | Financingavailable | 6 | James McAleney | Lorne Richards | K. K. Sangara | 1:45.78 | 
| 2006 | Financingavailable | 5 | James McAleney | Lorne Richards | K. K. Sangara | 1:44.57 | 
| 2005 | Schooner Bay | 4 | Emile Ramsammy | David R. Bell | Melnyk Racing Stables | 1:46.03 | 
| 2004 | Brass in Pocket | 5 | Todd Kabel | Robert P. Tiller | Frank Di Giulio, Jr. | 1:46.02 | 
| 2003 | Brass in Pocket | 4 | David Clark | Robert P. Tiller | Frank Di Giulio, Jr. | 1:45.98 | 
| 2002 | Brass in Pocket | 3 | Todd Kabel | Robert P. Tiller | Frank Di Giulio, Jr. | 1:43.21 | 
| 2001 | Moonlight Affair | 3 | Todd Kabel | Tino Attard | Stronach Stables | 1:45.19 | 
| 2000 | Katherine of Ascot | 4 | Constant Montpellier | Reade Baker | Terra Farm | 1:45.91 | 
| 1999 | Princess Alicia | 3 | Patrick Husbands | Sid C. Attard | Goldmart Farms | 1:45.15 | 
| 1998 | No Foul Play | 4 | Steve Bahen | Margaret A. Spencer | Margaret A. Spencer | 1:44.80 | 
| 1997 | Blue and Red | 5 | Rui Pimentel | Sid C. Attard | Jim Dandy Stable | 1:42.60 |