Chris Waller will be hoping to parlay a pivotal midweek win for Sydney's newly crowned premier jockey into new-season stakes success when He's Your Man contests the $100,000 Winter Challenge at Rosehill.

Waller trained the winner which gave James McDonald the outright lead in the 2013-2014 Sydney jockeys' premiership at the final meeting of the season on Wednesday.

It was only McDonald's sixth winner for Waller this season but the combination will like its chances of striking again with He's Your Man.

While other trainers had a greater influence on McDonald's successful premiership campaign, as a fellow New Zealander who has made a spectacular rise in Australian racing, Waller said he was happy to play a small part in the jockey's success.

"It's a proud moment, that's for sure, to be involved in a young person's career like James'," Waller said.

Waller said beating a jockey of Nash Rawiller's calibre for the title in only his second season in Sydney confirmed McDonald was a rider who was mature beyond his years.

"It's not just the city racing twice a week, it's all the other commitments that come with it," Waller said.

"It's no easy feat and I've got full respect for him for what he has achieved and there are a lot better things to come yet."

On a personal level for Waller, that could come as early as Saturday.

There are eight acceptors for the Winter Challenge and besides He's Your Man, Waller has Coup Ay Tee, I'm Imposing and Tougher Than Ever in the race.

Of the quartet, I'm Imposing has the best recent form as a last-start Randwick winner over 1600m and Tye Angland keeps the ride.

The rising nine-year-old returns to stakes racing for the first time since a photo-finish second to Zephyron in the Lord Mayors Cup at Rosehill on May.

But He's Your Man shapes as the most interesting runner of Waller's Challenge quartet.

A winner at Listed level in France last year, He's Your Man hasn't won in five Australian starts but his three placings for Waller include a first-up third to Generalife in the Civic Stakes at Rosehill.