Grand Slam winning jockey Jim Cassidy returns to race riding at Rosehill on Saturday, fresh from his annual winter break.

One of the senior figures in the Sydney jockeys' room, Cassidy is also one of its fiercest competitors.

He bagged five Group One victories in three states during 2012-13, a season he counts as among his best.

"I had as good a year last year as I have ever had really," Cassidy said.

"I'm feeling pretty good for a 50-year-old.

"I've got a few rides Saturday and it would be nice to bounce back with a winner."

During his break, Cassidy kept fit by swimming and maintaining his sprawling property.

He returned to trackwork riding just over two weeks ago and has also ridden in a handful of barrier trials to prepare for his race day return.

Physically, Cassidy feels in great shape.

Mentally, he is keen and looking forward to the challenge of another season.

"I wouldn't be coming back if I wasn't," he said.

Cassidy's five mounts on Saturday include Pretty Pins for John Thompson in the Listed Winter Challenge (1500m), the first stakes race of the new Sydney season.

The mare has been racing consistently without winning and made late ground to finish fifth to Under The Sun last start in a race dominated by the on-pace runners.

"I had a look at the video of her last run and she probably just wasn't suited by the tempo of that race," Cassidy said.

"If it's truly run, I think she'll run well."

Cassidy will team up with Chris Waller in three races.

He rides debutant Pinot Gris for the premier trainer in the opening event along with Velrosso in the TAB iPhone App Handicap (1200m) and Kristy Lee in the Become An ATC Sponsor Handicap (1100m).

Velrosso has an affinity with Rosehill where he has posted all three of his career wins.

Cassidy and Waller are also set to be a force into the spring with the hoop confirming he will reunite with Group One winner Hawkspur and smart youngster Zoustar when they make their seasonal returns.