2025 Highlander Stakes Preview

Key Takeaways:

• Patches O’Houlihan, Canada’s reigning Horse of the Year, is the 6-5 morning-line favorite and the one to beat with tactical speed, proven class, and a G2 turf win at the course and distance.
• My Boy Prince exits a strong second in the G1 Jaipur and brings top-tier form, good local credentials, and tactical speed that makes him a serious win threat.
• Dresden Row, consistently reliable and adaptable in pace scenarios, looms as a strong value play, especially with a proven record off layoffs and multiple graded placings.
• Playmea Tune and Old Chestnut both face questions—Playmea Tune must prove himself on turf, while Old Chestnut may struggle to repeat his front-end score against a faster field.

The 2025 Highlander Stakes at Woodbine Racetrack on Saturday, June 28, features eight of the best older horses in Canada. The race is an intriguing mix of horses better proven on the lawn and ones who are better known for what they’ve done on the main track, including reigning Canadian Horse of the Year Patches O’Houlihan and King’s Plate runner-up My Boy Prince.

The Highlander Stakes began as the Highlander Handicap at Greenwood Park in 1954 and moved to Woodbine in 1957. Originally a dirt race, the Highlander was moved to the lawn in 2004. Some of its best winners over the years include Canadian Horses of the Year Canadiana (1955), Play the King (1987), and Soaring Free (2004, 2005).

Highlander Stakes Information

• Race Date: Saturday, June 28
• Track: Woodbine Racetrack in Etobicoke, Ontario
• Post Time: 5:06 p.m. Eastern Daylight Time
• Distance: six furlongs on the E. P. Taylor outer turf course
• Age/Sex: four-year-olds and up
• Where to Watch: FanDuel TV
• Where to Bet: FanDuel Racing

2025 Highlander Stakes Draw and Odds

These are the eight horses running in the 2025 Highlander Stakes, including their post positions, trainers, jockeys, and morning-line odds.

Highlander Stakes Prep Race Results

All eight entrants in the Highlander come out of different races.

Three of the runners come out of graded stakes. My Boy Prince comes out of the Jaipur (G1) on Belmont weekend at Saratoga, where he finished a close second behind Ag Bullet. The other two come out of Grade 3 wins at Woodbine: Ms. Tart upset fillies and mares in the Royal North on the grass, while Old Chestnut wired the Jacques Cartier on the Tapeta.

Three others come out of ungraded stakes. Patches O’Houlihan began his season with a win in the Thorncliffe on May 25 over the local Tapeta. Two others come from stakes on the Turfway Tapeta: Playmea Tune won the Forego at 6 ½ furlongs on February 1, and Dresden Row was second by a head in the Prairie Bayou going 1 1/16 miles there December 14.

The other two runners come out of allowance races on the inner turf at Woodbine. Its Time to Shine crossed the wire second but was placed third in a five-furlong, second-level sprint June 12, and Niagara Skyline was fourth in a third-level race going 7 ½ furlongs on June 1.

Highlander Stakes Contenders

This is the field for the 2025 Highlander Stakes, from the rail out:

1. My Boy Prince: Though he didn’t win last out, he comes out of the classiest race—the Grade 1 Jaipur at Saratoga—and finished a close second. The extra half furlong should help him, and he won at that distance at Aqueduct two races back. With tactical speed, good Woodbine form, and high-percentage connections, he shapes as one of the major contenders.
2. Playmea Tune: This Josie Carroll trainee, a lightly-raced five-year-old, is a wild card. He loves six and a half furlongs on the Tapeta, but ran off the board in his only try on the grass. That said, that turf try was the Woodbine Mile (G1), a tougher race than this, and he was beaten only four lengths all told. Both Carroll and jockey Rafael Hernandez are having strong seasons at Woodbine, and if this class and distance on the turf suit him, he is good enough to run well at a square price.
3. Niagara Skyline: The turn back from 7 ½ furlongs to six furlongs should help this War Dancer gelding. However, he does his best racing on or very close to the lead, meaning he’ll have company the way this field set up. Class is also a question; he often brings good efforts in allowance company, but would need a career best to run with the top contenders in this graded-stakes race.
4. Its Time to Shine: A fixture in the starter-optional ranks, he won at that level going six furlongs on the Tapeta to start the season, graduated to a win in first-level allowance company going five and a half, and then was placed third after crossing the wire second in a five-furlong turf dash against second-level company. This is another step forward, though, and he has yet to run a race that would threaten the best here—he would need a major step up from his career best to be any more than a pace factor.
5. Patches O’Houlihan: The defending Canadian Horse of the Year, he won his return in an ungraded dash at 5 ½ furlongs on Tapeta on May 4. He shapes as the speed of the speed, and though he won’t be alone, he has proven time and again that he can battle and keep on running. He is more proven on the all-weather than he is on the turf, but in his only recent try on the grass, he won the Nearctic (G2) last October over this course and distance. In short, he’s not invincible, but he’s the horse to beat.
6. Ms. Tart: She is cross-entered in the Nassau (G2) against fillies and mares as well as this race against males. Though the Nassau is sex-restricted, the distance of this race will suit her better. She would still need a step up from that effort to be a contender here, but if the pace gets hot (which it very well may), she could make a run for a piece.
7. Old Chestnut: Facing a field of just three in the Jacques Cartier, jockey Eswan Flores did the smartest possible thing with Old Chestnut—send him to the front and dare the rest to catch him. No one could. He can run a decent race from off the front end, though his wins tend to come when he flukes into the lead. With as much pace as there is in this race, don’t expect him to make the top—instead, if he doesn’t bounce to the moon after that big race last out, he has a shot to clunk on to complete a trifecta or superfecta.
8. Dresden Row: This four-year-old colt is a model of consistency for Lorne Richards, never off the board in ten starts. That includes three runs in graded company at Woodbine last year. He can run a winning race from the front end, a stalking spot, or even a little further back from that, giving him the versatility he needs to handle the outside. And, though he hasn’t raced since December, he returned a winner off a similar layoff last year.

Highlander Stakes FAQ

Q: When is the Highlander Stakes?

A: The Highlander Stakes happens on Saturday, June 28. The eighth race on the Woodbine card, first post is set for 5:06 p.m. Eastern Daylight Time.

Q: Where is the Highlander Stakes?

A: The Highlander Stakes is run at Woodbine Racetrack in Etobicoke, Ontario.

Q: Which trainer has the most wins in the Highlander Stakes?

A: Lou Cavalaris, Jr. leads all trainers with four wins in this race between 1959 and 1977. Among trainers who have a horse in the 2025 edition of the race, Mark Casse (My Boy Prince) leads with two – he won in 2023 with Lucky Score and 2024 with Filo Di Arianna.

Q: Who is the favorite for the Highlander Stakes?

A: The 6-5 morning-line favorite for the Highlander Stakes is Patches O’Houlihan. The reigning Canadian Horse of the Year and a graded winner on both Tapeta and turf, he will likely hold as the favorite in the race.

Q: Who is the best Highlander Stakes jockey?

A: Todd Kabel leads all jockeys with four wins in the Highlander between 1997 and 2005. Among riders entered in 2025, the only one who has won before is Sahin Civaci, who won in 2023 with Lucky Score.

Q: Who won the Highlander Stakes in 2024?

A: Filo Di Arianna won the Highlander in 2024 for trainer Mark Casse and jockey Kazushi Kimura. Kimura does not ride in the race this year, though Casse sends out My Boy Prince with jockey Sahin Civaci.

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