Two sets of racing silks made famous in two different eras of Australian racing have left their mark on Sydney's first race meeting of the year.

Nepean and Cassadee both produced wins on Monday that had their respective stables tipping bright futures for the three-year-olds.

The James Cummings-trained Nepean carried colours worn by Leilani, a top-class stayer trained by his grandfather Bart during the 1970s, to win the Happy New Year Plate.

Leilani was so good to Bart, he named his Randwick stables Leilani Lodge and his grandson continues the family tradition out of the yard which has been home to some of Australia's turf greats.

But there is more than the symbolic connection that Cummings hopes will carry Nepean to greater heights.

Nepean was bred by his grandfather as a son of the 12-time Melbourne Cup-winning trainer's Australian Derby winner Roman Emperor.

"I remember looking at Nepean as a yearling with my grandfather in the paddocks at Princes Farm," Cummings said.

"He's the son of a Group One winner from the stable and he was bred on the banks of the Nepean River."

Gai Waterhouse thinks it's time she had another Australian Oaks winner.

And in first-up winner Cassadee, Waterhouse might have a filly to train on through the summer and into the autumn.

Cassadee is raced by prominent breeder George Altomonte and his Corumbene Stud colours have been synonymous with major wins, including Overreach's 2013 Golden Slipper victory.

"She could be an Oaks filly in the making," Waterhouse said.

In a win straight out of the Tulloch Lodge manual, Cassadee ($4.60) sat close to the lead before striding clear to win by 2-1/4 lengths in the TAB Maiden Plate.

"I liked the way when once she hit the front she wanted to come right away," Waterhouse said.