What is the Highlander Stakes?
The Highlander Stakes is a Grade II Thoroughbred race held annually at Woodbine Racetrack in Toronto, Ontario, Canada. Contested at 6 furlongs on the turf for horses aged three and older, it is the premier turf sprint in Canada and one of the most competitive six-furlong turf races in North America. Inaugurated in 1954 as the Highlander Handicap at Toronto's Greenwood Raceway, the race moved to Woodbine in 1957 and switched from dirt to turf in 2004. The race was upgraded to Grade I status in 2018 before being downgraded to Grade II in 2022. The Highlander Stakes has a tradition of attracting top international turf sprinters, particularly from the United States, Australia, and Europe, making it one of the most globally competitive races in Canadian racing. Soaring Free won back-to-back editions in 2004 and 2005 to become the most celebrated recent dual winner. The speed record of 1:07.13 was set by Long On Value in 2018. Wesley Ward, Mark Casse, and Brad Cox have been the dominant trainers in recent editions. Woodbine's E.P. Taylor turf course, known for its unique three-turn configuration, tests horses differently than standard oval turf courses and rewards versatile sprinters.
When is the Highlander Stakes in 2026?
The 2026 Highlander Stakes is scheduled for late June at Woodbine Racetrack. Contested at 6 furlongs on the turf with a purse of $250,000, the race draws the top turf sprinters from North America and internationally.
Highlander Stakes History & Notable Winners
The Highlander Stakes has attracted some of the top turf sprinters in North America in recent years. Patches O'Houlihan gave trainer Robert Tiller and jockey Sofia Vives a 2025 win in 1:08.39 for longtime owner Frank Di Giulio Jr. — the same connections that won the race back in 2003 with Forever Grand. Filo Di Arianna (BRZ) gave trainer Mark Casse and jockey Kazushi Kimura a 2024 victory in 1:09.75 for owner Gary Barber, the Brazilian-bred mare adding another Canadian graded stakes win to her impressive resume. Lucky Score gave Casse and Kimura a 2023 victory in 1:07.86, the fastest recent renewal. Bound For Nowhere made history in 2022 by winning at age eight under Pablo Morales for trainer-owner Wesley Ward, one of the oldest horses to win a graded stakes race in Canadian racing history. Silent Poet gave trainer Nicholas Rodriguez and jockey Justin Stein a 2021 win in 1:07.98 for Stronach Stables.
| Year | Winner | Jockey | Time |
|---|---|---|---|
| 2025 | Patches O'Houlihan | Sofia Vives | 1:08.39 |
| 2024 | Filo Di Arianna (BRZ) | Kazushi Kimura | 1:09.75 |
| 2023 | Lucky Score | Sahin Civaci | 1:07.86 |
| 2022 | Bound For Nowhere | Pablo Morales | 1:08.01 |
| 2021 | Silent Poet | Justin Stein | 1:07.98 |
The Highlander Stakes is the premier turf sprint in Canada and one of the most internationally competitive six-furlong turf races in North America each summer.
