The Whimsical Stakes is a thoroughbred horse race run annually in mid April at Woodbine Racetrack in Toronto, Ontario, Canada. A Grade III race since 2006, it is open to fillies and mares aged four and older. It is raced over a distance of 6 furlongs on Tapeta synthetic dirt and currently carries a purse of $115,500.
Since its inception in 1956 at Toronto's Greenwood Raceway, the race has been contested at various distances: 6 furlongs : 1956 at Greenwood Raceway, 1975 at Fort Erie Racetrack, 1976–1979, and since 1986 at Woodbine Racetrack furlongs : 1957 at Greenwood Raceway, 1968-1974 at Fort Erie Racetrack 7 furlongs : 1958-1960, 1980-1985 at Greenwood Raceway 1 mile : 1961-1966 at Greenwood Raceway 1 mile : 1967 on turf at Fort Erie Racetrack
The race was run in two divisions in 1981 and 1984.
Records Speed record: (at current distance of 6 furlongs) 1:08.35 - Boardroom (2021)
Most wins: 3 - Prospective Dolly (1991, 1993, 1994)
Most wins by an owner: 3 - Estate of M. Rich & N. Clements (1991, 1993, 1994) 3 - Larkin Maloney & Conn Smythe (1958, 1959, 1960) 3 - Stafford Farm (1966, 1976, 1979) 3 - Sam-Son Farms (1983, 1988, 2017)
Most wins by a jockey: 6 - Dave Penna (1984, 1987, 1988, 1991, 1993, 1994) 6 - Patrick Husbands (2000, 2006, 2012, 2018, 2023, 2024)
Most wins by a trainer: 5 - Mark E. Casse (2012, 2018, 2022, 2023, 2024)
Winners of the Whimsical Stakes Year Winner Age Jockey Trainer Owner Time2026Reagan's Flame5Sahin CivaciSaffie A. Joseph Jr.BAG Racing Stables, Turf Express and Watkins Diamond Stables1:10.112025Earhart (FR)4Rafael Manuel HernandezJoise CarrollLNJ Foxwoods1:08.842024Play the Music4Patrick HusbandsMark E. CasseGlassman Racing LLC1:10.592023Our Flash Drive5Patrick HusbandsMark E. CasseLive Oak Plantation1:10.122022Our Secret Agent5Kazushi KimuraMark CasseGary Barber1:09.622021Boardroom4Luis ContrerasJosie CarrollLNJ Foxwoods1:08.352020Jean Elizabeth5David MoranLarry RivelliR Ravin, Patricia's Hope & L Rivelli1:09.862019Shakopee Town4Alan GarciaKevin AttardAl & Bill Ulwelling1:09.552018Let It Ride Mom4Patrick HusbandsMark CasseLive Oak Plantation1:08.962017Southern Ring5Eurico Rosa Da SilvaMalcolm PierceSam-Son Farm1:09.702016Leigh Court6Florent GerouxMichael StidhamSpeedway Stable1:08.882015Unspurned4Alan GarciaRoger L. AttfieldChristine Hayden1:09.182014Purely Hot6Chantal SutherlandTevis Q. McCauleyUnlimited Equine1:09.892013Acting Naughty4Tyler PizarroDonald C. MacRaeJohn Hillier1:09.762012Roxy Gap4Patrick HusbandsMark CasseEugene Melnyk1:09.152011Wildcat Marie4Tyler PizarroMartin DrexlerBaldesarra & Partners1:09.112010Proud Heiress6Chantal SutherlandWayne MoggeMichael Cavey.1:09.712009Dancing Allstar4James McAleneyTerry JordanBob Cheema1:09.162008My List4Eurico Rosa Da SilvaNicholas GonzalezTucci Stables1:09.712007Seductively4Gerry OlguinIan BlackKinghaven Farms1:12.272006Abounding Truth6Patrick HusbandsJosie CarrollDouglas Kent Racing1:10.552005Nashinda4David ClarkMacdonald BensonAugustin Stable1:11.802004Holy Bubbette4Joe BravoDavid FawkesKatherine Elam1:10.372003Brass In Pocket4David ClarkRobert P. TillerFrank DiGiulio, Jr.1:12.692002 Mysterious Affair5Dale HemsleyJ. Mort HardyJ. Mort Hardy1:10.542001Mysterious Affair4Richard Dos RamosJ. Mort HardyJ. Mort Hardy1:11.782000Barlee Mist5Patrick HusbandsWray I. LawrenceBarlee Farm1:10.481999Barlee Mist4Michael QuongWray I. LawrenceBarlee Farm1:10.621998Bimini Blues5Sandy HawleyMichael MattineTheodore F. Burnett1:10.601997Eseni4Mickey WallsPhil EnglandKnob Hill Stable1:10.001996Fleet Wahine5Robert LandryFrank A. Passero, Jr.Frank Stronach1:11.001995Showering4Emile RamsammyMichael MattineTheodore F. Burnett1:10.401994Prospective Dolly7Dave PennaTony MattineEst. M. Rich/N. Clements1:09.801993Prospective Dolly6Dave PennaTony MattineEst. M. Rich/N. Clements1:10.801992Family Investment4Todd KabelMichael J. DoyleL. S. Moore1:12.201991Prospective Dolly4Dave PennaTony MattineEst. M. Rich/N. Clements1:12.401990Diva's Debut4Richard Dos RamosDebbie EnglandHuntington Stud Farm1:10.001989Zadracarta4Sandy HawleyPat CollinsKnob Hill Stable1:11.001988Ruling Angel4Dave PennaJames E. DaySam-Son Farm1:11.601987Dice Cup4Dave PennaDavid R. BellJohn A. Franks1:11.401986Quitman4David ClarkTony MattineE. H. Curnes1:11.401985Dancing Emerald5Brian SwatukSheldon WolfeL. & D. Lee1:26.401984Mrs. Specklewing4Dave PennaAlton QuanbeckNorcliffe Stables1:26.201984Dancing Emerald4Robert King, Jr.Sheldon WolfeL. & D. Lee1:26.001983Tiffany Tam4Irwin DriedgerJames E. DaySam-Son Farm1:27.001982Eternal Search4Gary StahlbaumEdward MannJim Dandy Stable1:27.001981Sober Jig4J. Paul SouterYonnie StarrJean-Louis Levesque1:26.001981Lacey4David ClarkFrank H. Merrill, Jr.W. P. Gilbride/O'Connell1:26.601980Kennisis5Gary StahlbaumGlenn MagnussonG. Vasey & D. Finn1:24.401979Royal North4Robin PlattsGil RowntreeStafford Farm1:10.401978Polder Pie5Sandy HawleyM. R. ClarkM. R. Clark1:10.201977Reasonable Win5Avelino GomezFred H. LoschkeHammer Kopf Farm1:10.401976Gurkhas Band4Robin PlattsGil RowntreeStafford Farms1:09.801975Lovely Sunrise4Colin BainDonnie WalkerConn Smythe1:11.201974Miss Rebound6Sandy HawleyGilbert H. RobillardGrovetree Stable1:16.801973Sonny Says Quick8Gregg McCarronOdie ClellandPeter D. Fuller1:20.401972Main Pan4Gregg McCarronOdie ClellandPeter D. Fuller1:16.601971Not Too Shy5Richard GrubbDonnie WalkerConn Smythe1:17.401970Anxious Age7James KellyAndrew G. SmithersG. W. Bydson1:18.801969Double Ripple4Eldon NelsonJohn Tammaro, Jr.V. Mosca1:18.601968Anxious Age5Clifford PottsPaul CooperG. W. Brydson1:19.001967Ice Water4Avelino GomezLou Cavalaris, Jr.Gardiner Farm1:47.201966Sharon Market4Avelino GomezCarl F. ChapmanStafford Farms1:38.201965Battling Way6Eric WalshN. FletcherN. Fletcher1:40.201964Sky Diver4James FitzsimmonsJerry C. MeyerEdward B. Seedhouse1:38.201963Twice Shy4Ron TurcotteJerry C. MeyerH. Waggoner1:39.001962Scratch Off4Jim ParnellJerry C. MeyerD. Mann1:39.001961Menantic4James FitzsimmonsGordon J. McCannWindfields Farm1:37.801960Wonder Where4Clifford PottsYonnie StarrMaloney & Smythe1:29.401959Kitty Girl5Al CoyYonnie StarrMaloney & Smythe1:25.401958Kitty Girl4R. GonzalezYonnie StarrMaloney & Smythe1:25.201957Saragino4Edward PlesaArthur H. WarnerLanson Farm1:21.401956Willies Folly4Ernie WarmeJerry C. MeyerR. Papa1:12.00
See also List of Canadian flat horse races
References