| Class: | Restricted Stakes |
| Horse Race: | Classy 'N Smart Stakes |
| Location: | Woodbine Racetrack Toronto, Ontario, Canada |
| Inaugurated: | 1997 |
| Race Type: | Thoroughbred - Flat racing |
| Distance: | 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.
Speed record:
Most wins:
Most wins by an owner:
Most wins by a jockey:
Most wins by a trainer:
| 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 |