Irish apprentice Tom Sherry is starting to hit his straps in Sydney but it took a pep talk from boss Mark Newnham to help him keep the faith.

Sherry was to the fore at Randwick on Saturday claiming a Highway Handicap win aboard the Gary Colvin-trained Another One before combining with Newnham to score on Gone Bye.

But his year has not all been smooth sailing.

After cutting his teeth on the country and provincial circuits last term, Sherry was given the green light by Newnham to ride predominantly in town this season.

Finding himself in one of the most competitive jockeys' rooms in the world, Sherry made tough going of it at first.

"That first month was really difficult for him because it didn't come as easily as people thought it might," Newnham said.

"Look, part of me was pleased it didn't. I tried to explain to him leading into this season it wasn't going to be as easy for him as it was going through the provincial ranks.

"After a couple of meetings his head was down and I said to him, 'you will be right once you get your confidence'."

That confidence is starting to come and so are the winners.

Almost five months into the season Sherry is the leading metropolitan apprentice, putting him in the box seat to join another of Newnham's proteges, Robbie Dolan, who has won the title for the past two years.

"Apart from being a very good jockey, he is a very good young man, similar to Robbie Dolan," Newnham said.

"They are good, hard-working young fellas who want to succeed and appreciate the opportunity they have got here."

Sherry's win on Gone Bye was extra special as the horse is owned by Newnham's office manager, Maureen Chalmers and her family.

It was the horse's fifth victory from 14 starts and his first in Saturday grade and Newnham described Gone Bye as a great bread and butter horse.

"Those sort of horses is what gets owners involved and keeps people in Sydney racing," he said.

"We need the headline horses but you need horses like that who dig in for the contest.

"They earn a lot of prize money over a career and you get to enjoy them."

A little like Sherry himself this season, Gone Bye ($3.70) had to dig deep to get the result.

After trailing the leader, the gelding got the upper hand and staved off all challengers to score a dogged short neck win over Parry Sound ($11) with Trevelyan ($18) the same margin away third.

"It was a tough effort. It's very hard for a horse to do all the work, have the others get to him then pull it out of the bag and get his head in front," Sherry said.

Newnham later notched a double of his own when Big Parade, ridden by Josh Parr, streeted his Heineken Handicap rivals.