2025 bet365 Highlander Stakes (G2T) – Race Preview & Analysis
Date: June 28, 2025
Track: Woodbine Racetrack
Race: Race 8
Distance: 6 Furlongs (Turf)
Purse: CA$200,000
Eligibility: 4-Year-Olds & Up
Post Time: 4:32 PM ET
Contenders Breakdown
1. My Boy Prince
Pedigree: Cairo Prince – Hopping Not Hoping
Trainer: Mark E. Casse
Jockey: Sahin Civaci
Analysis: Runner-up in the G1 Jaipur at Saratoga, this 4YO gelding returns to his home base where he’s been ultra-consistent. Cairo Prince adds turf versatility, and his front-running style suits this configuration. Major win contender.
2. Playmea Tune
Pedigree: Maclean’s Music – Fifth Overture
Trainer: Josie Carroll
Jockey: Rafael Hernandez
Analysis: Stakes winner at Turfway Park, this 5YO gelding has tactical speed and a strong turf pedigree. Maclean’s Music adds brilliance, and Carroll is a top turf conditioner. Could be a value play.
3. Niagara Skyline
Pedigree: War Dancer – Expressly Yours
Trainer: John Charalambous
Jockey: Dylan Davis
Analysis: Veteran 7YO gelding with a grinding style. War Dancer adds turf stamina, but he’s likely overmatched in this field. Best used underneath.
4. Its Time to Shine
Pedigree: Souper Speedy – Platinum Steel
Trainer: John A. Ross
Jockey: Jose Luis Campos
Analysis: Lightly raced 4YO colt with upside. Souper Speedy is a strong Ontario sire. Could surprise if he gets a clean trip.
5. Patches O’Houlihan
Pedigree: Reload – Maythefourthbwithu
Trainer: Robert P. Tiller
Jockey: Sofia Vives
Analysis: 12-time winner at Woodbine and reigning G2 Nearctic champ. Missed the G3 Jacques Cartier due to a fever but returned with a dominant win in the Thorncliffe Stakes. The 6-5 morning-line favorite and the one to beat.
6. Ms. Tart
Pedigree: Maximus Mischief – Sheza Sweet Lemon
Trainer: Kevin Rice
Jockey: Huber Villa-Gomez
Analysis: Winner of the G3 Royal North last out. Maximus Mischief is a rising sire, and this filly has tactical speed. Cross-entered in the G2 Nassau but dangerous if she runs here.
7. Old Chestnut
Pedigree: Speightstown – Pool Land
Trainer: Martin Drexler
Jockey: Eswan Flores
Analysis: 8YO gelding who won the G3 Jacques Cartier last out. Speightstown is a top turf sprint sire. Veteran presence with a late kick—must use in exotics.
8. Dresden Row
Pedigree: Lord Nelson – Elle Special
Trainer: Lorne Richards
Jockey: Ryan Munger
Analysis: G3 winner with a strong closing style. Lord Nelson adds sprint brilliance. Could be flying late if the pace heats up.
Top Picks:
Win Contender: Patches O’Houlihan – local hero, elite turf sprint form
Main Rival: My Boy Prince – G1-placed, tactical speed
Value Play: Old Chestnut – sharp recent win, proven class
Exacta Box: Patches O’Houlihan, My Boy Prince, Old Chestnut
Trifecta Add-On: Dresden Row – late closer with upside
