It's not often considered a head-scratching race when a reigning Canadian Horse of the Year wins over a strong field that includes two other Canadian champions, but that's exactly what happened Saturday in the GII Bet365 Highlander Stakes at Woodbine. Sure, 4-5 choice Patches O'Houlihan (Reload) won, just like he was supposed to, but it was the manner in which he won–veering out badly–that left perhaps more questions than answers.
As a precaution after pulling up, he was vanned back to his barn and examined by veterinarians. It was quickly discovered Patches O'Houlihan suffered a soft-tissue injury. No long-term prognosis was immediately available, but the gelding and fan favorite was reportedly resting comfortably.
In his first start of 2025, Patches O'Houlihan won the 5 1/2-furlong Thorncliffe Stakes by four lengths, setting a new synthetic track record of 1:02.28 at Woodbine while getting a 108 Beyer Speed Figure, the highest of the year to date in North America on synthetic. He then missed a scheduled start in the GIII Jacques Cartier Stakes when he spiked a fever, but he missed little training time. The gelding switched to the grass for the Highlander, a surface which had netted a previous win for him on the GII Nearctic Stakes last October. In addition to his Horse of the Year title, Patches O'Houlihan has twice been named Canada's champion male sprinter. He's won nine black-type events, six graded.
In the Highlander, Patches O'Houlihan went right to the front, as is his custom, while last-out GI Jaipur Stakes second My Boy Prince (Cairo Prince) chased from second. The champ set a first quarter pace of :22.13, but going into the turn, regular rider Sofia Vives looked uncomfortable, as if she were applying the brakes, with her arms and legs extended far in front of her torso. 'Patches' veered out just after he rounded the turn, opening up a huge hole to his inside, which My Boy Prince took advantage of and quickly looked as if he might catch the eventual winner, eventually getting within a head. Down the stretch, Patches O'Houlihan continued to drift badly–finally running closer to the grandstand than the rail–but held sway by a neck and a huge heart as My Boy Prince also drifted and swapped to his wrong lead. While all eyes were on the first two, the eventful race concluded with MGSW Dresden Row (Lord Nelson), who was supplemented to the Highlander, in third, giving the three Canadian champions the trifecta.
Pedigree Notes:
Patches O'Houlihan is one of six black-type winners–two graded–for Reload, a son of Hard Spun who stands at Northern Dawn Stables in Ontario. The Highlander winner and runner-up are both out of daughters of Silent Name (Jpn), who also stands in Ontario at Adena Springs North.
Maythefourthbwithu has a 2-year-old colt by Souper Speedy and a yearling full-brother to Patches O'Houlihan. All have been bred by Frank D. Di Giulio, Jr., who also campaigns Patches O'Houlihan as a homebred.
#5 PATCHES O'HOULIHAN ($3.60) drifted through the stretch but still couldn't be beaten in the $200,000 Highlander Stakes (G2) at @WoodbineTB. @SofiaLVives was aboard the five-year-old Reload gelding for trainer Robert Tiller. pic.twitter.com/S3fMQrtVXU
— FanDuel Racing (@FanDuel_Racing) June 28, 2025
Saturday, Woodbine
BET365 HIGHLANDER S.-GII, C$234,400, Woodbine, 6-28, 4yo/up, 6fT, 1:08.39, gd.
1–PATCHES O'HOULIHAN, 124, g, 5, by Reload
1st Dam: Maythefourthbwithu, by Silent Name (Jpn)
2nd Dam: Cat's Calling, by Caller I. D.
3rd Dam: Jazzie Jagua, by Tom Cat
O/B-Frank D. Di Giulio, Jr. (ON); T-Robert P. Tiller; J-Sofia
Vives. C$144,000. Horse of the Year-Can, Ch. Male Sprinter
(twice)-Can, Lifetime Record: 16-13-1-0, $853,848.
Werk Nick Rating: C. Click for the
eNicks report & 5-cross pedigree or the free
Equineline.com catalogue-style pedigree.
2–My Boy Prince, 120, g, 4, Cairo Prince–Hopping Not
Hoping, by Silent Name (Jpn). (C$115,000 Ylg '22 CANSEP).
O-Gary Barber; B-Murray Graham Smith (ON); T-Mark E.
Casse. C$48,000.
3–Dresden Row, 122, c, 4, Lord Nelson–Elle Special, by
Giant's Causeway. ($11,000 Ylg '22 KEEJAN; $70,000 2yo '23
OBSAPR). O-True North Stable and Bloom Racing Stable
(Jeffrey Bloom); B-TCR Ranch (KY); T-Lorne Richards.
C$22,000.
Margins: NK, 3, HD. Odds: 0.80, 2.25, 8.70.
Also Ran: Playmea Tune, Niagara Skyline, Old Chestnut. Scratched: Its Time to Shine, Ms. Tart.
Click for the Equibase.com chart or the TJCIS.com PPs. VIDEO, sponsored by FanDuel TV.
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