Sydney's leading trainer Chris Waller has amassed 300 winners in a season for the first time as the milestones continue to mount for the Australian Racing Hall Of Fame inductee.

Success through In Times Of War on the Gold Coast enabled Waller to post a triple century nationwide then Chatelard produced his 168th Sydney metropolitan winner at Rosehill to leave Waller two victories short of eclipsing the mark he set in 2015-16.

"When I started training, I was hoping to get a thousand winners. I thought if I did that I'd be remembered," he said on Saturday.

"I've been very fortunate. We've taken some good opportunities and I'm grateful for the support I get from owners and staff. They're just as proud as I am."

Chatelard ($6.50) paired up with in-form jockey Tye Angland at Rosehill to claim the Winter Racing Handicap (1800m) by a short neck from $5.50 favourite Kurnel Jaxon.

The Waller-trained Vaucluse Bay ($6.50) was the same margin back in third.

Waller was pleased to see Chatelard nail the fourth win of his career second-up after the gelding's previous campaign was underwhelming.

"I guess last preparation he was a little bit disappointing because he did show us quite a bit prior to that," he said.

"It's good to see him come back so well and I think he'll improve again up over 2000 metres."