A Grade 2 event, the Highlander Stakes was first run in 1954 at Woodbine. Run at six furlongs on turf, the race is held for horses 3-years and older. Six horses have won the race twice since 1976 with Sam-Son Farm winning it six times as an owner and both jockey Todd Kabel and Lou Cavalaris winning it four times each. In 2017, the Highlander Stakes was added to the Breeders' Cup Challenge "Win and You're In" Series as a qualifier for the Turf Sprint.
A Grade 2 event, the Highlander Stakes was first run in 1954 at Woodbine. Run at six furlongs on turf, the race is held for horses 3-years and older. Six horses have won the race twice since 1976 with Sam-Son Farm winning it six times as an owner and both jockey Todd Kabel and Lou Cavalaris winning it four times each. In 2017, the Highlander Stakes was added to the Breeders' Cup Challenge "Win and You're In" Series as a qualifier for the Turf Sprint.