In a huge weekend for the stable, Pepper will also saddle up four runners at Thoroughbred Park on Sunday afternoon.

But its the $76,000 Highway that would really put a spring in his step.

Pepper is chasing a fourth win on the trot with Affinity Beyond, who returned from a 46-week spell last month in flying fashion and took out a Class 2 Handicap at Wagga Riverside.

The Canberra trainer has stuck with his winning formula and given jockey Simon Miller the ride, hoping to complete the quadruple on her Sydney debut.

"We're really looking forward to seeing her head to the big smoke and have a crack at some really good prize money," Pepper said.

"She's super. She's a very gifted mare and came back from a long spell and won first up for us. She deserves her chance at the Highway on Saturday.

"I'd rather be training her than any other horse in the race. We're looking forward to seeing her step up and hopefully she can go as well as we hope she would."

Pepper claimed a Benchmark50 Handicap (1200 metres) at Queanbeyan Racecourse with Tycoon Tily on Thursday, beating Theresa Bateup's Halliday Road by 0.35 lengths.

Halliday Road held the lead from 800 metres, before Tycoon Tily took off and chased him down the outside following the turn.

It was the five-year-old's fourth win for the stable, with Pepper hoping it'll boost her confidence after a slow start this preparation.

"I was quite happy with her, she's been quite disappointing in previous runs," Pepper said.

"She probably hasn't shown us her true ability at the races this preparation, she's been thereabouts without winning. Just really happy to see her win."