It took an examination of the photo finish to confirm Streaking Comet's win but after a delay the filly was declared the first city winner for the new Cummings partnership.
Bart and his grandson James, who has worked with the master for the past few years, entered into the new venture at the beginning of the month and had a winner at Kembla Grange last week.
But the honour of the first Randwick win goes to the daughter of Northern Meteor who put her nose down to edge out Electric Power in the opening event over 1400 metres which was named in honour of jockey Simone Montgomerie who died in a race fall in Darwin earlier this week.
Stewards inspected the photo finish before confirming the judge's decision.
James Cummings was on hand to greet the filly who is raced by the Gooree Syndicate which recently lost its young stallion Northern Meteor to colic.
"It is very special to have our first city winner and to have had that here at Randwick," Cummings said.
"Bart has been training here for over thirty years now and this is his first winner here in partnership and I am very proud.
"The partnership has taken its time. Bart does not do anything in a rush and he has probably been thinking about it since May last year perhaps.
"In the last few months it has gained headway and here we are. It all seems so quick."
The young trainer was fulsome in his praise of Streaking Comet who was joined by Jim Cassidy aboard runner-up Electric Power 100 metres out and fought hard to the line.
"She had to give three-and-a-half kilos to the horse who just went down to her, not to mention that the Pumper was there giving his best to get one over us so she is a very gutsy filly, very tough, and a great credit to her sire who is unfortunately not with us anymore," he said.
"She has a bright future and she has knocked over a Saturday race for her owners."