Jim Cassidy is no stranger to Toorak Handicap success and is chasing his fifth win in the Group One race at Caulfield.

Cassidy first won the Toorak in 1991 on Comrade and has since added victories on Marble Halls (1998), Umrum (2000) and Red Dazzler (2006).

This year he rides the Chris Waller-trained Strawberry Boy, a last-start fourth in the Group One Sir Rupert Clarke Stakes (1400m) at Caulfield after pressing forward from a wide barrier.

Strawberry Boy has another wide gate on Saturday with the second outside barrier in the field of 17 but Cassidy believes the gelding can give a sight on the speed.

"Overall his run was good second-up and third-up on Saturday he should be cherry ripe," Cassidy said.

"He has a bad barrier again but he'll probably roll forward. He's a bulldog, he likes a fight up front. So he'll take it to them and be honest again.

"It's been a good race to me the Toorak. And once again I've got a nice ride in it."

Cassidy's book of Group One rides on Saturday also features Payroll in the Thousand Guineas, a race the jockey has won three times, and Shards in the Caulfield Guineas.

Cassidy has claimed two Caulfield Guineas including a memorable victory on Redoute's Choice 16 years ago when he defeated Testa Rossa.

Meanwhile, Stratum Star rises 2.5kg in the Toorak on his Sir Rupert Clarke Stakes win but jockey Craig Williams is counting on a better favourable barrier draw in gate two and the confidence gained from the narrow last start Group One win to offset that.

"The barrier draw is much more favourable to him and he's going to really enjoy the 1600 metres," Williams said.

"But he has to still step up because he's gone up two-and-a-half kilos."

Williams chose Stratum Star over Noble Protector in the Toorak.

Noble Protector was unplaced over 1400m first-up in the Let's Elope Stakes but will be out to bounce back over 1600m with Michael Walker to ride.

"If I end up being wrong and she does win, I'll be the first to say I was wrong and congratulate them," Williams said.

Disposition, beaten in a photo by Stratum Star last start, is just shading Lucky Hussler for favouritism with Stratum Star at $7.