Anna Jeffs Handicaps the Plate Trial and Woodbine Oaks

With The King’s Plate only one month away, 3-year-old hopefuls have a chance this weekend to prove their right to challenge for Canada’s premier race of the year.

Some top Canadian-bred colts and geldings will run in the Plate Trial and the best fillies will contest the Woodbine Oaks this Sunday.

Both races have produced recent King’s Plate winners, including 2023 Plate Trial winner Paramount Prince, and Moira, 2022 winner of the Woodbine Oaks.

Moira, trained by Kevin Attard, went on to win the 2024 Maker’s Mark Breeders’ Cup Filly & Mare Turf Grade 1 and the 2024 Champion Turf Female Eclipse Award.

In 2024, My Boy Prince won the Plate Trial and Caitlinhergrtness came second in the Woodbine Oaks.

They then met in The King’s Plate where Caitlinhergrtness went on to become the second filly in three years to win the $1 million classic.

On Sunday, we have a great group of Canadian three-year-olds entered for the Trial and the Oaks.

Let’s do some handicapping.

Plate Trial – Sunday, Race 9

Top Selection: #6 Highwaytothemoon – This front runner out of Ransom the Moon had the best Beyer figure of the year of this 12-horse field with an 85 after a win in the Queenston Stakes. He has come out of his last race with a great work over 5 furlongs in :57.4 on June 27 and two further maintenance works since. Although his sire is more of a sprinter, he has won over longer distances. With Woodbine’s 2025 top jockey Rafael Hernandez taking the mount on Highwaytothemoon over other King’s Plate hopeful Casson, this colt is set up for success.

Wildcard: #11 Powell River – He has raced only once at Woodbine, breaking his maiden in a Maiden Special Weight on June 14th. Most of the other top contenders in this field have faced each other in races, but Powell River is a newcomer. As a front runner in the 11-hole, this colt out of the most recent American Triple Crown winner Justify will require an ideal trip. He only has three races under his belt and has raced just once on an all-weather track. Ryan Munger has the mount and he will surely be eager to defend his victory from last year, winning the Plate Trial with Sedburys Ghost. If you don’t like the favourite, Powell River presents a promising alternative.

Longshot: #8 Fire and Wine – Fire and Wine has not shown much this season, however, had a strong finish to the 2025 season. He won the Coronation Futurity Stakes in November with an 86 Beyer, which is the highest of any horse in this field. With a bullet in his most recent work, perhaps he can return to his form from last year.

The Play: $10 to WP on #6 Highwaytothemoon.  

Woodbine Oaks – Sunday, Race 10

Top Selection: #7 Luster – This filly out of Knicks Go has proven to be effective in route races, including in her most recent win in the Grade 3 Selene Stakes. She is in good shape coming out of her last race with a bullet for her most recent work with stablemate Bold Time. Luster likes to sit just off the pace and has National Museum of Racing and Hall of Fame jockey John Velazquez in the saddle. Velazquez also guided her to victory at Keeneland in April. Interestingly, Velazquez won the Oaks on No Time last year, though Luster is arguably in better condition coming into this race.

Wildcard: #1 Piper’s Gift – She has proven effective on the all-weather track, winning all four starts on the surface, so please disregard her turf performances – it does not seem to be her preferred surface. This daughter of Yorkton is new to the mix, having only ever run against Katie’s Grace, while most of the others have raced numerous times against each other. With jockey Rafael Hernandez taking this mount rather than Dixie Law, she will be a force to be reckoned with.

Longshot: #6 Bold Time – This filly, trained by Josie Carroll, who also trains Luster, is a solid longshot with a chance with strong works and may benefit from the extra distance. This daughter of Not This Time, who produced No Time, last year’s Oaks winner, needs a clean break, after an awkward break last time out. She may benefit from a fast pace. Reunited with jockey Fraser Aebly, who piloted her to victory to break her maiden, the pair may just prove her critics wrong.

The Play: 5$ WPS on #1 Piper’s Gift, $3 exacta on Piper’s Gift/Luster, $2 exacta on Luster/Piper’s Gift.