Chiefswood had three Canadian-breds in the race - Roscar, Saccharine and Side Street - and they finished one-two-three.
134th Breeders' Stakes
The two-year-old filly by Medaglia D'Oro won Woodbine's Catch a Glimpse Stakes and goes for the Miss Grillo Stakes.
The OLG Canadian Triple Crown wraps up on Sunday with a small field, minus the King's Plate and Prince of Wales winners.
Vitality, the Prince of Wales Stakes winner, and the filly Hurricane Clair will be the top contenders in the marathon event.