Story by Mathew Toogood – Racing.com

Jaylah Kennedy with Berkeley Square after winning the Ronald McDonald House Charities Trophy at Flemington Racecourse on September 14, 2024 in Flemington, Australia. (Photo by Brett Holburt/Racing Photos)

Apprentice Jaylah Kennedy is a chance to bring up a milestone first Stakes victory when she continues her association with in-form Berkeley Square in the Coongy Cup at Caulfield on Wednesday.

Kennedy, who is indentured to Berkeley Square’s trainer Dan O’Sullivan, has only ridden in three Stakes races so far, all at Listed level, without winning.

But two-straight victories aboard Berkeley Square at Flemington and Sandown in recent weeks have earned Kennedy her chance to try to add a Stakes victory in Wednesday’s Group 3 race.

“She’s done nothing wrong on the horse and the horse seems to be going well for her,” O’Sullivan said.

“She believes in the horse and he knows her quite well. So we’ll stick with that plan.”

The Coongy (2000m) has attracted a field of nine, with Berkeley Square among the leading contenders in early markets and he is set to jump from the outside barrier.

“You’ve got to go where the races are, but I’d like it to have been at Flemington or Sandown,” O’Sullivan said.

“But the race is at Caulfield, so we’ll deal with that.”

Berkeley Square has won once from eight attempts at Caulfield, with another three placings.

O’Sullivan said Kennedy had confidence to get the job done on Berkeley Square from back in the field last start and he was delighted to see the way the galloper overhauled his rivals in the straight.

“He really attacked the line strongly,” he said.

“He’s come through it fantastic and he’s getting out now to what I believe to be his best distance at 2000 metres-plus.

“He’s quite well in at the weights and he’s getting better and better in the coat all the time. He’s not quite there 100 per cent yet, but a few more consistent warm days, he’ll be there.”

O’Sullivan wants to get through the Coongy before deciding the next spring target for Berkeley Square but said the Bendigo Cup is ‘probably the logical one’.

Races such as the Geelong Cup, Moonee Valley Cup or even the JRA Plate at The Valley are among the other options.

A few days after Berkeley Square runs in the Coongy, promising filly Too Darn Discreet will be out to enhance her VRC Oaks credentials in Saturday’s G3 Ethereal Stakes (2000m) at Caulfield.

Too Darn Discreet has pieced together a pair of wins – over 1500m and then in the G2 Edward Manifold Stakes over 1600m – in her past two starts and O’Sullivan said stepping to 2000m, with a view to progressing towards the Oaks, is the logical way to go.

“At this stage we’ll build towards the Oaks,” he said.

“It’s interesting, there’s only 10 fillies looking for the 2000 metres (in the Ethereal), so come Oaks time, too, there might not be many left there. We’ll head down that path and work our way through it.”

O’Sullivan, however, has the option to drop Too Darn Discreet back in distance after the Ethereal if he doesn’t believe the Oaks trip is going to suit.

“She’s still a developing filly and if I had any thought that she’s not going to get the Oaks trip, we can just freshen her up and come back to the Thousand Guineas,” he said.

Michael Dee has been booked to ride Too Darn Discreet on Saturday.

“She’s trained on really well from her last start at Flemington,” O’Sullivan said.