The Highlander Stakes is a Thoroughbred horse race run annually at Woodbine Racetrack in Toronto, Ontario, Canada. Run in mid to late June, the Grade II race is open to horses aged three and older. Raced over a distance of six furlongs on turf, it currently offers a purse of $250,000.

Inaugurated in 1954 as the Highlander Handicap at Toronto's Greenwood Raceway, it was moved to Woodbine Racetrack in 1957. The race was contested on dirt through 2003 when it was moved to the turf for the 2004 edition. It has been run at a distance of six furlongs except for 1957 and 1958 when it was run at seven furlongs.

The race was upgraded to Grade II status for 2010, fell to a Grade III, and restored as a Grade II event in 2014. In 2018, the Jockey Club of Canada moved it to Grade I status.

The event was downgraded to Grade II in 2022.

Records Speed record: 1:07.13 - Long On Value (2018)

Most wins: 2 - Signature Red (2010, 2011) 2 - Stutz Bearcat (1979, 1980) 2 - Wake At Noon (2000, 2002) 2 - Soaring Free (2004, 2005) 2 - Smart Enough (2007, 2009)

Most wins by an owner: 6 - Sam-Son Farm (1973, 1978, 1979, 1980, 2004, 2005)

Most wins by a jockey: 4 - Todd Kabel (1997, 2003, 2004, 2005)

Most wins by a trainer: 4 - Lou Cavalaris, Jr. (1959, 1964, 1969, 1977)

Winners Year Winner Age Jockey Trainer Owner Time2026Miss Vyvyanne6Pietro MoranGail CoxRalph R. Murray and Calstar Farm0.56.272025Patches O'Houlihan5Sofia VivesRobert P. TillerFrank D. Di Giulio, Jr.1:08.392024Filo Di Arianna (BRZ)8Kazushi KimuraMark E. CasseGary Barber, Wachtel Stable and Peter Deutsch1:09.752023Lucky Score5Sahin CivaciMark E. CasseGary Barber, Pantofel Stable, LLC and Wachtel Stable1:07.862022Bound For Nowhere8Pablo MoralesWesley A. WardWesley A. Ward1:08.012021Silent Poet6Justin SteinNicholas RodriguezStronach Stables1:07.982020Not run due to the COVID-19 pandemic.2019Wet Your Whistle4Alex CintronMichael J. TrombettaDavid W. Palmer1:07.882018Long On Value7Florent GerouxBrad H. CoxMadaket Stables, Ten Strike Racing, Steveh Laymon1:07.132017Green Mask6Javier CastellanoBrad H. CoxAbdullah Saeed Almaddah1:07.592016Passion for Action4Eurico da SilvaMichael P. De PauloBenjamin Hutzel1:08.052015Go Blue or Go Home6Alan GarciaReade BakerSusan & Jim Hill1:07.182014Something Extra6Eurico da SilvaGail CoxMenary/Cox1:07.782013Go Blue Or Go Home4Luis ContrerasReade BakerSusan & Jim Hill1:10.462012Smokey Fire7Eurico da SilvaSid AttardJim Dandy Stable1:07.772011Signature Red5Luis ContrerasSid AttardNorseman Racing Stable1:09.002010Signature Red4Chantal SutherlandSid AttardNorseman Racing Stable1:08.172009Smart Enough6Jeremy RoseJohn FisherEdith R. Dixon1:08.262008Heros Reward6Javier Castellano Dale Capuano Rob Ry Farm/Jayne Marie Slysz1:08.022007Smart Enough4Patrick HusbandsJohn FisherEdith R. Dixon1:08.532006Marco Be Good4Justin SteinJohn A. RossTerra Farm1:07.872005Soaring Free6Todd KabelMark FrostadSam-Son Farm1:08.032004Soaring Free5Todd KabelMark FrostadSam-Son Farm1:08.722003Forever Grand4Todd KabelRobert P. TillerFrank DiGiulio Jr.1:09.532002Wake At Noon5Emile RamsammyAbraham KatryanBruno Schickedanz1:09.722001Mr. Epperson6James McKnightScott H. FairlieR. & S. Fairlie et al.1:10.652000Wake At Noon3David ClarkAbraham KatryanBruno Schickedanz1:10.381999Vice N' Friendly4Mickey WallsAbraham KatryanS. Sesook & D. Yarush1:09.081998Cocney Lass3Neil PoznanskyDarren GlennonRainbow End Racing et al.1:09.601997Glanmire7Todd KabelMike KeoghKenny, O'Leary et al.1:09.401996Love Grows4Robert Landry Roger AttfieldKinghaven Farms1:09.601995Le Magister4Dave Penna Bernard GiraultI. Jamieson1:10.401994Swamp King *4Robert Landry Frank MontroseRidge Rock Farm1:09.801994End Sweep *3Chris McCarronKathy Patton-CasseHarry T. Mangurian Jr.1:09.801993Premier Angel4Robert Landry Dennis M. ErwinWilliam A. Sorokolit Sr.1:10.801992King Corrie4Dave PennaSherry NoakesAubrey W. Minshall1:09.601991Key Spirit5Mickey WallsStephen BarnesBig Bux Stable1:10.801990Native Factor3Brian SwatukPhil EnglandFrank Stronach1:09.801989Mr. Hot Shot4Jim McAleneyWilliam StewartJ. Stewart / M. Upton1:09.201988Highland Ruckus3David ClarkTony MattineLinmac Farms1:09.401987Play The King4Don SeymourRoger AttfieldKinghaven Farms1:09.201986Near The Storm4Dan BeckonJack ReidRose Hill Farms1:10.601985Centenarian4Brian SwatukFrank H. Merrill Jr.Est. C. E. Pickering1:10.401984Introspective3Jack LauzonJohn Tammaro Jr.Kinghaven Farms1:09.401983Fraud Squad4Dan BeckonBill MarkoEdward B. Seedhouse1:09.801982Great Gladiator5Larry AttardSteve AttardTom Campbell1:10.601981Solo Guy3Brian SwatukLaurie SilveraGordon F. Hall1:08.801980Stutz Bearcat5George HoSangJames E. DaySam-Son Farm1:09.201979Stutz Bearcat4George HoSangJames E. DaySam-Son Farm1:09.601978Casanova Kid5Richard GrubbJames E. DaySam-Son Farm1:09.801977One Pound Sterling5Jeffrey FellLou Cavalaris Jr.Gardiner Farm1:10.001976Gurkhas Band4Robin PlattsGil RowntreeStafford Farms1:10.001975Island Fling4Sandy HawleyJerry G. LavigneParkview Stable1:10.201974Pocket Measure4James KellySamuel G. DixonJ. O. Pallett1:11.201973Don't Ask Me That3Gary StahlbaumArthur H. WarnerSam-Son Farm1:10.001972Briartic4James KellyAndrew SmithersBennett Farms1:09.401971Coup Landing6James KellyAndrew SmithersCalvin H. Sturrock1:10.001970Muzledick5Richard GrubbJ. Mort HardyPrime Acres Stable1:10.401969James Bay5Johnny SellersLou Cavalaris Jr.Gardiner Farm1:10.801968No Reasoning5Wayne ChambersJerry G. LavigneParkview Stable1:11.001967Chillicoot5Ronnie FerraroStan U. RossBlue-C-Stable1:09.601966E. Day6Noel TurcotteHume E. M. PollockHume E. M. Pollock1:10.801965Royal Tara4John LeBlancGlenn MagnussonStafford Farms1:10.401964Vindent de Paul6P. MaxwellLou Cavalaris Jr.Hillcrest Stable1:10.601963Kisco Kid5Harlon DaltonGeorge C. FrostadGeorge C. Frostad1:10.401962Its Ann6Harrel BolinW. MoorheadG. R. Woodrow1:10.601961Anita's Son5Hugo DittfachArthur H. WarnerLanson Farm1:09.201960Tyhawk5W. MarshLes LearSinger & Lear1:10.201959War Eagle5Clifford PottsLou Cavalaris Jr.P. Del Greco1:10.601958Mister Jive4Johnny LongdenGeorge M. CarterJ. L. Applebaum1:22.001957Nirdar4Al CoyJohn J. ThorpeJ. E. Frowde Seagram1:23.401956Jimminy Baxter6Pat RemillardJames C. BentleyB. R. Steen1:10.601955Canadiana5T. JohnsonGordon J. McCannE. P. Taylor1:11.201954Kentario6A. NashJohn CalhounGreen Valley Stable1:10.20

* In 1994 there was a dead heat for first.

See also List of Canadian flat horse races

References

The Highlander Stakes at Pedigree Query The 2007 Highlander Stakes at Woodbine Entertainment