Stamping himself as the top 2-year-old colt in Ontario, Philip My Dear came from far off the pace to take the $251,600 turf race.
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Inducted into the Canadian Horse Racing Hall of Fame this year, Keogh is the last Triple Crown-winning trainer.
While Peter Brant's Rougir recovered from trouble, Canadian-bred Moira barges her way to second only to be disqualified.
Emma-Jayne Wilson guided the Mark Casse trainee to victory – the gelding's third in as many outings at Woodbine.
The 85th edition of the 1 1/16-mile event for Canadian-bred 2-year-olds runs over the E.P. Taylor Turf Course.
Older horses will travel 1 1/16 miles on the Tapeta in the Durham Cup including Buttigieg Training Centre's Artie's Storm.
Ontario-bred Grade 1 winner Silent Poet will meet Highlander Stakes winner Bound for Nowhere in Oct. 8 turf dash.
Induction ceremonies for the Class of '22 will be held in the summer of 2023, along with those inducted as part of the Class of '23.
The magic victory involved an 8-year-old mare, winless in '22, trained by a 95-year-old and ridden by a young jock who had never won a race.
The Queen's Plate and Woodbine Oaks winner will try turf and older horses in the Grade 1 E.P. Taylor at Woodbine on Oct. 8.
