At Canterbury on Wednesday, he had a city double when the aptly-named The Special Two and Nazir delivered the young trainer victories but the day could have ended twice as well with Shahrazad and Burning Passion going down in close finishes.
On Saturday it's very much the old and the new for the Leilani Lodge stable with Cummings's two runners, Precedence and Ruling Dynasty, resuming from a spell.
Ruling Dynasty, a lightly-raced staying prospect, will kick off his spring in the LUCRF Jockeys Trust Benchmark 80 Handicap (1600m).
In Ruling Dynasty's first campaign he won two races and the preparation culminated with a respectable 3-3/4 length defeat in the Australian Derby after overcoming a foot abscess in the lead-up to the three-year-old feature.
"He's come back a more refined, athletic type of horse,” Cummings said. "There's a lot more tone and less puppy fat on him.
"We've been on the back foot getting him ready for the spring because we were in a holding pattern with a potential sale to Hong Kong.
"There were unforeseen complications in the sale so Gooree decided to call it off and retain him.
"He was a bit behind for his trial but since then he's come along in leaps and bounds.”
With last Sunday's passing of Cummings's legendary grandfather and co-trainer Bart, James knows all eyes will be on him in this year's lead-up to the Melbourne Cup.
Ruling Dynasty and Precedence are the stable's most likely Melbourne Cup prospects but the young horseman isn't getting ahead of himself with Ruling Dynasty.
"He's a genuine staying horse and that's why he's kicking off in a 1600 metre race,” he said.
"What is his target? He's entered for the Melbourne Cup but being realistic he's a benchmark 75 horse so a lot of things need to happen for us to even get close to a race like that.
"We'll just take things as they come to us and see where he takes us.
"The horse is naturally going to improve off Saturday's run but I'm confident he'll run well.”
Precedence has lined up in four previous Melbourne Cups and on Saturday he kicks off his quest for a fifth start in Australia's greatest horse race in the Group II Chelmsford Stakes (1600m).
"His gallop last Saturday at Randwick was excellent,” he said. "He's a marvel, I honestly think he's going as well as he ever has.
"He's going to get back on Saturday and there doesn't look to be too much tempo in the race but in the event the pace is genuine, he'll be warming up and getting home past more than will be getting past him.
"I think he'll produce a really honest run.”