A familiar milestone for Chris Waller could also come with a stable first for the season as the champion trainer closes in on another century of winners.

Waller sits third on the national premiership with 98 wins and there's an outside chance he might reach triple figures during racing on Friday despite limited numbers at provincial meetings in NSW and provincial.

Since arriving as a serious force in Australian racing during 2008/2009, Waller has trained no less than 136 winners in each subsequent season, culminating in 228 victories in 2013/14.

If Waller can't train his 100th winner on Friday, he will be at almost unbackable odds to do so on Saturday with multiple runners in most Randwick races and chances at Kembla Grange as well as at Flemington.

And it could easily be one of four two-year-olds Waller has engaged in the Hyland Race Colours Plate at Randwick which might provide reason for double celebrations.

Waller has yet to train a two-year-old winner this season but it's a statistic that will hardly cause panic for a trainer who prides himself on patience.

This was never more evident than when he ended last season as Australia's leading two-year-old trainer despite not leading in a juvenile winner until February.

Bookmakers rate unraced Bernadini colt Gigolo the best of Waller's quartet with the barrier trial placegetter sharing the second line of favouritism behind Godolphin's Holler.

Waller had two juvenile placegetters in Sydney and Melbourne last week in a result that the trainer said was a sign his team of young horses was ready to make an impact.

"I think that gives us a good benchmark for where we at at. We are not far away with our two-year-olds," Waller said.

"I don't mind this colt (Gigolo)," Waller said. "He trialled well, he's got plenty of speed."

Waller said an 1100-metre race for a two-year-old's first start presented a challenge.

"We'll hope he gets the 1100 (metres) first-up ... he's a pretty good colt."

Gigolo is a $4.60 chance in early markets with Encosta Line and Flaunting rated the next best of Waller's runners at $15.

Waller has three early favourites for Randwick - dual acceptor Good Project (race one), Georgey Aeroplane (race four) and You'll Never (race five).