The decision to bypass Melbourne's winter finals day at Flemington has reaped an immediate reward for apprentice Regan Bayliss.

The chance to stick with one of his favourite horses, Kenjorwood, swayed the 18-year-old to come to Randwick on Saturday to ride for his boss Peter Moody.

Kenjorwood did however, give Bayliss a few anxious moments when he wobbled around the turn and needed to be persuaded to go straight in the opening race, the Shoot Out Mile.

"I could have had three rides but Kenjorwood is one of my favourites and I'm thankful to Mr Moody for bringing me here," Bayliss said.

"It means a lot to win. It's my first time in Sydney.

"I walked the track before the race and spoke to Blake Shinn who helped me a lot.

"The horse wanted to do a few things wrong but it was a pretty soft win in the end."

Bayliss settled Kenjorwood ($2.60) near the tail of the five-horse field and brought him wide on the turn where the horse tried to go even wider.

Bayliss got him back under control and he raced to a two length win over the favourite Pajaro ($2.25) with a neck to Eigelstein ($5).