One of the most anticipated riding stints in Sydney racing in recent seasons begins in earnest at Rosehill on Saturday.

The Run To The Rose meeting will be apprentice John Kissick's first metropolitan outing under the guidance of premier Sydney trainer Chris Waller.

Kissick has been one of the best apprentices in NSW for several seasons and he arrives in Sydney with his 3kg city allowance well and truly intact.

One of his two rides for his new boss will be the in-form Velrosso in the James McCall Retirement Handicap (1300m).

Chasing a hat-trick, Velrosso will be one of the favourites to extend his winning sequence but Waller doesn't expect the moment to faze the 22-year-old.

"He's had a taste of city racing before and he's ridden a couple of winners for us so the pressure is off in my opinion," Waller said.

"John is a mature boy and we've kept it as simple as we can for him because Velrosso is a straightforward horse. He gets back and he runs home.

"He will be a worthy apprentice to have over the next three months."

Kissick has been indentured to Leeton trainer Peter Clancy and for the past 12 months he has attracted the attention of leading stables in Sydney and Melbourne without making a permanent move.

He will also ride accomplished stayer Marden for Waller in the TAB Rewards Handicap (2400m) while he will partner Just A Girl for Warwick Farm trainer Scott Aspery in the Sportsyear Handicap (1100m).

Kissick resumes riding after a suspension with three mounts at Newcastle on Thursday.