The Grey Stakes is a Canadian Thoroughbred horse race held annually during the first week of October at Woodbine Racetrack in Toronto. A Grade III, it is open to two-year-old horses and is raced on dirt at a distance of miles. Since 2006, the dirt racing surface at Woodbine Racetrack has been the synthetic Polytrack.
Inaugurated as the Grey Stakes at the Old Woodbine Racetrack in 1906, it was named in honor of the then Governor General of Canada, Earl Grey. Over the years it has been run at various distances: 1 mile : 1906-1929 (Old Woodbine Racetrack) 1 mile 70 yards : 1930-1955 (Old Woodbine Racetrack) miles : 1956 to present at Woodbine Racetrack
J. K. L. Ross, owner of the first United States Triple Crown Champion, Sir Barton, won this race five years in a row with future U.S. Racing Hall of Fame trainer, Henry McDaniel. In 1926 Henry McDaniel added another win, making him the leader among all winning trainers.
Notable horses who have won the race include future Canadian Horse Racing Hall of Fame inductees Horometer (1933), Kennedy Road (1970), Sunny's Halo (1982), and Sky Classic (1989). Dancer's Image won the 1967 race and went on to capture the following year's Kentucky Derby, as did Mine That Bird in 2009. Since the creation of the Breeder's Cup races in 1984, Macho Uno is the only horse to have won the Grey Stakes then gone on to win that year's Breeders' Cup Juvenile.
Famous horses who did not win the Grey Stakes include Display who ran second in 1925 but was the ensuing year's Preakness Stakes winner. As well, the 1997 Belmont Stakes winner Touch Gold finished third in the 1996 running of the Grey Stakes.
Records Time record: (at current miles distance) 1:43.20 - Black Cash (1997)
Most wins by an owner: 5 - J. K. L. Ross (1921, 1922, 1923, 1924, 1925) 5 - Sam-Son Farm (1984, 1986, 1987, 1989, 2004)
Most wins by a jockey: 5 - Pat Remillard (1937, 1943, 1947, 1961, 1963) 5 - Dave Penna (1982, 1986, 1987, 1992, 1995)
Most wins by a trainer: 6 - Henry McDaniel (1921, 1922, 1923, 1924, 1925, 1926)
Winners of the Grey Stakes since 1956 Year Winner Jockey Trainer Owner Time2025The Big Con (GB)Sahin CivaciMiguel ClementReeves Thoroughbred Racing, Tony Weintraub and Brandon M. Dalinka1:46.572024He's Not JokingKazushi KimuraJosie CarrollDi Scola Boys Stable1:43.182023Two GhostsJustin SteinBarbara J. MinshallHoolie Racing Stable LLC1:44.562022Bluebirds OverEdgard J. ZayasSaffie A. Joseph Jr.Edward Seltzer & Beverly Anderson1:45.322021God of LoveRafael M. HernandezMark E. CasseEclipse Thoroughbred Partners & Gary Barber1:44.202019ChapaluPatrick HusbandsArnaud DelacourEA Seltzer & BS Anderson1:44.502018SolidifyEmma-Jayne WilsonReade BakerPaul Braverman & Timothy Pinch1:43.902017ArchaggelosRafael M. HernandezMichael W. DickinsonMonticule LLC1:44.562016Golden HawkPatrick HusbandsMark E. CasseLive Oak Plantation1:43.382015RikerJesse M. CampbellNicholas GonzalezTucci Stables1:44.312014International StarRafael M. HernandezMichael J. MakerKenneth & Sarah Ramsey1:45.152013Ami's HolidayLuis ContrerasJosie CarrollIvan Dalos1:44.802012River SevenEurico Rosa Da SilvaNicolas GonzalezTucci Stables1:43.982011ProspectiveLuis ContrerasMark E. CasseJohn C. Oxley1:44.552010Blue LaserCorey FraserMark E. CasseWinStar Farm1:45.782009Bear Tough GuyEurico Rosa da SilvaReade BakerBear Stables1:45.342008Mine That BirdChantal SutherlandDavid CoteyDavid Cotey, D. Ball & HGHR Inc.1:44.452007GlobetrotterJeremy RoseH. Graham MotionEarle I. Mack1:46.592006Skip CodePatrick HusbandsMark E. CasseCharles Laloggia1:45.562005UnificationRobert LandryEoin G. HartyDarley Stable1:46.502004Dance with RavensTodd KabelMark FrostadSam-Son Farm1:47.792003SmoocherJim McAleneyDavid R. BellJohn A. Franks1:46.742002WandoRichard MiglioreMichael KeoghGus Schickedanz1:45.102001ChangeintheweatherMickey WallsDavid R. BellPin Oak Stable1:47.032000Macho UnoJerry D. BaileyJoe OrsenoStronach Stable1:44.131999Four On The FloorPatrick HusbandsAlexander McPhersonLor Stables1:45.121998Certainly ClassicConstant MontpellierAlexander McPhersonDominion Bloodstock et al.1:46.201997Black CashRobert LandryDaniel J. VellaFrank Stronach 1:43.201996Cash DepositTodd KabelDaniel J. VellaFrank Stronach 1:45.001995GomtuuDave PennaDominic J. PolsinelliTri-Colour Racing Stable1:46.601994Talkin ManRobert LandryRoger AttfieldKinghaven Farms & Helen G.Stollery1:46.601993Road RushRobert LandryDaniel J. VellaFrank Stronach1:46.001992Truth Of It AllDave PennaSheldon WolfeA. Schmidt1:46.201991Steady RiseMickey WallsRoger AttfieldKinghaven Farms1:47.401990Wildy SpecialArt Madrid, Jr.Stephen L. DiMauroRobert J. Sullivan1:46.201989Sky ClassicSandy HawleyJames E. DaySam-Son Farm1:46.001988Mercedes WonLloyd DuffyArnold FinkChris Spencer1:45.601987Regal ClassicDave PennaJames E. DaySam-Son Farm1:45.001986Blue FinnDave PennaJames E. DaySam-Son Farm1:47.401985Bishop BobDavid ClarkArthur H. WarnerVictura Farm1:47.801984Dauphin FabuleuxJeffrey FellJames E. DaySam-Son Farm1:45.401983Ten Gold PotsGary StahlbaumGil RowntreeB. K. Y. Stable1:45.001982Sunny's HaloDave PennaDavid C. Cross Jr.David J. Foster1:45.401981Tampa Bay BuckDan BeckonArnold FinkJohn Spencer1:46.001980BayfordRobin PlattsJohn J. Tammaro, Jr.Kinghaven Farms1:44.201979Sunny PremierGary StahlbaumFrank H. Merrill, Jr.Meadowview Stable1:46.201978Port EbonyGeorge HoSangM. ClappertonS. C. S. Stable 1:44.401977Cash the TicketW. WoodsJ. KellyM. Martin1:52.801976Do LishusChris RogersSheldon WolfeKrever Farm1:47.201975Bay StreakDavid ClarkGordon M. HuntleyWhittaker Stable1:47.401974SilverbatimJeffrey FellGordon M. HuntleyMutual Enterprises1:44.801973Trojan BronzeRobin PlattsGlenn MagnussonA. B. Roks1:46.401972ImpecuniousJ. MoseleyGeorge HandyMrs. R. L. Feinberg1:44.001971Spirit RockBrian SwatukGil RowntreeStafford Farms1:44.401970Kennedy RoadSandy HawleyJames C. BentleyHelen G. Stollery1:47.201969Dance to MarketChris RogersEarl HarbourneV. Martin Jr.1:52.601968Jumpin Joseph Brian SwatukRobert S. BatemanWarren Beasley1:46.801967 Dancer's Image Avelino GomezLou Cavalaris, Jr.Peter D. Fuller1:48.201966Pine PointAvelino GomezJerry C. MeyerWillow Downs Farm1:45.201965Titled HeroAvelino GomezPatrick MacMurchyPeter K. Marshall1:47.201964Des ErablesJohn LeBlancDuncan R. CampbellMrs. S. Thomas1:48.401963Ramblin RoadPat RemillardGordon M. HuntleyGordon F. Hall1:45.001962Sound StageGeorge GubbinsJohn PasseroStafford Farms1:44.201961Admiral GanoPat RemillardAlfred I. TaylorDon G. Ross1:45.201960Belle O McClure John R. AdamsHarry TrotsekHasty House Farm1:45.201959Eltoro The GreatGeorge GubbinsJohn PasseroWilliam R. Beasley1:50.401958 Anita's SonC. M. ClarkArthur H. WarnerLanson Farm1:48.801957SalonBillie FiskJ. BrownI. Tenney1:47.401956Roman ArtistEegene A. RodriguezJohn PasseroWilliam R. Beasley1:45.00
In 1963 Bimini Bill finished first but was disqualified and set back to second. In 1999 Exciting Story won but was disqualified and placed fifth.
Earlier winners
1955 - Compactor 1954 - Senator Jim 1953 - King Maple 1952 - Avella 1951 - I'm Sandy 1950 - Argyle 1949 - Mighty Nice 1948 - Avona 1947 - Dymoke 1946 - Watch Wrack 1945 - Hyperhelio 1944 - Dune 1943 - Green Bush 1942 - Gallant Foe 1941 - Air Sure 1940 - Jascarf 1939 - Second Helping 1938 - Peterhof 1937 - Poona 1936 - Aldwych 1935 - Abbatoro 1934 - Brannon 1933 - Horometer 1932 - Tractable 1931 - Dark Mission 1930 - Irish Maiden 1929 - Sweet Sentiment 1928 - Butter John 1927 - Solace 1926 - Willie K. 1925 - Penstick 1924 - Caduceus 1923 - Turnberry 1922 - Prismar 1921 - Marble 1920 - Our Flag 1919 - No race (World War I) 1918 - No race (World War I) 1917 - No race (World War I) 1916 - Arravan 1915 - Candle 1914 - Lady Curzon 1913 - Hodge 1912 - Leochares 1911 - Aldebaran 1910 - Picolata 1909 - Penn 1908 - Arondack 1907 - Dredger 1906 - Glimmer
See also Road to the Kentucky Derby List of Canadian flat horse races