My Boy Prince, Patches O’Houlihan to Duel at Woodbine

My Boy Prince , fresh off a runner-up performance in the Jaipur Stakes (G1T) earlier this month at Saratoga Race Course, returns to familiar turf June 28 at Woodbine to race six furlongs in the CA$200,000 Highlander Stakes (G2T).

The multiple stakes-winning 4-year-old son of Cairo Prince , trained by Mark Casse for owner Gary Barber, has experience on both the Woodbine synthetic main track and turf, though he has yet to run in his native Canada this year. In May, My Boy Prince started 2025 with a hard-fought win in the Elusive Quality Stakes at Aqueduct Racetrack.

Another Highlander contender, the 2024 Canada Horse of the Year, Patches O’Houlihan , won the June 4 Thorncliffe Stakes on synthetic before being scratched from the May 31 Jacques Cartier (G3), which would’ve been the Reload gelding’s second start of the year.

Patches O’Houlihan was running a high temperature the morning before the race; trainer Bob Tiller suggested to owner and breeder Frank Di Giulio Jr. that the horse was too sick to race.

“Regardless of the disappointment, doing right by the horse is all that matters,” Di Giulio said. “He’s okay now, and that is the main thing.”

Six others are entered against My Boy Prince and Patches O’Houlihan, though one of those, the Ontario-bred filly Ms. Tart , is cross-entered in the CA$175,000 Nassau Stakes (G2T), a mile race on turf restricted to fillies and mares.

The Highlander and Nassau are among five stakes on the Saturday program.

Entries: bet365 Highlander S. (G2T)

Woodbine, Saturday, June 28, 2025, Race 8

Grade IIT
6f
Turf
$200,000
4 yo’s & up
5:06 PM (local)

Caitlinhergrtness Brings Hot Hand into Nassau

2024 King’s Plate Stakes winner and fellow Ontario-bred Caitlinhergrtness headlines the Nassau. The Sovereign Award-winning 3-year-old filly of last year, who showed in the Queen Elizabeth II Challenge Cup Stakes (G1T) at Keeneland in the fall, captured the May 31 Belle Mahone Stakes (G3) by five lengths at Woodbine to kick off her 4-year-old campaign.

Kevin Attard trains the WinStar Farm-owned daughter of Omaha Beach , who is favored at 2-1 odds on the morning line over Resolute Racing’s United States shipper Sweet Rebecca , trained by Chad Brown, at 3-1.

Ms. Tart is projected as a 15-1 shot if she starts in the 12-horse Nassau. She is 20-1 on the morning line for the Highlander.

Entries: bet365 Highlander S. (G2T)

Woodbine, Saturday, June 28, 2025, Race 8

Grade IIT
6f
Turf
$200,000
4 yo’s & up
5:06 PM (local)

Marine Stakes

As race 5 on the card, the first of the day’s stakes is the CA$150,000 Marine Stakes (G3) for 3-year-olds, featuring Church and State , who has run strongly in his young career, winning three of four starts. Most recently, the gray and/or roan gelding legged out a victory in the May 8 King Corrie Stakes.

Scorching , an Ontario-bred colt and a leading early prospect for this summer’s King’s Plate, makes his 2025 debut. He won twice in three starts last year, all of which were at Woodbine.

Four others in the 1 1/16-mile synthetic race are Ontario-breds, including Megalodon , who has finished first or second in three of four starts this year, with the blemish being an 11th-place finish in the American Turf (G1T) at Churchill Downs.

Entries: HPIbet Marine S. (G3)

Woodbine, Saturday, June 28, 2025, Race 5

Grade III
1 1/16m
All Weather Track
$150,000
3 yo
3:24 PM (local)

Selene Stakes

A field of eight 3-year-old fillies will duke it out in the CA$150,000 Selene Stakes (G3). The speedy Serendipity recorded a win and one runner-up in two starts in the U.S. for trainer Brad Cox, and now competes for Canadian trainer Josie Carroll.

Nata Trouble , runner-up in four of her last five starts, exits a swiftly run Fury Stakes and seeks an elusive victory. The bay filly has been winless since Sept. 2024.

The Selene, like the Marine, is contested at 1 1/16 miles on Woodbine’s synthetic Tapeta surface.

Entries: Selene S. (G3)

Woodbine, Saturday, June 28, 2025, Race 7

Grade III
1 1/16m
All Weather Track
$150,000
3 yo Fillies
4:32 PM (local)

Dominion Day Stakes

The longest stakes race on Saturday is the 1 1/8-mile, CA$150,000 Dominion Day Stakes (G3) for older horses, which lured 10-time-winning mare Fashionably Fab , who battles seven male rivals in the race over synthetic.

Essex Support and Classic Mo Town both were victorious in their lone Woodbine appearances this year. The former, who last year as a 3-year-old took the 2024 Marine, captured and allowance optional claimer last month, while the latter rallied to victory in the May 31 Eclipse Stakes (G2).