The Cambridge trainer has the daughter of Proisir set for Saturday's Gr.1 Vinery Stud Stakes (2000m), an age group feature at Rosehill that he won back in 2002 with Sixty Seconds.
"I remember it very well, my memory's not failing and it would be lovely to do it all over again," James said.
He now operates in partnership with Robert Wellwood, and Prowess will bid to hand the duo their second Group One success on Australian soil following Pinarello's win last season in the Queensland Derby (2400m).
"She arrived here on Sunday and was dripping from head to toe when she got off the float, but it was 32 degrees," James said.
"Honestly, top marks to her as she has now really settled in incredibly well at Randwick. We're pretty happy with her."
Prowess , who will be ridden by Mark Zahra, sealed her trip with an impressive last start defeat of the older horses in the Gr.1 New Zealand Stakes (2050m) at Pukekohe.
Freshened after finishing third in the Gr.1 New Zealand 2000 Guineas (1600m), she is unbeaten this preparation following her first-up success in the Gr.2 Auckland Guineas (1600m).
Prowess then claimed the Listed Karaka Million 3YO Classic (1600m) and the Gr.2 David & Karyn Ellis Fillies' Classic (2000m) before the New Zealand Stakes.
James and Wellwood have also celebrated top-flight victories with Concert Hall in the Gr.1 Zabeel Classic (2000m) and Two Illicit in the Gr.1 Captain Cook Stakes (1600m) since forming a partnership at the beginning of the 2018-19 season.
Wellwood initially joined Kingsclere Stables in 2017 in the role of Racing Manager before taking out his trainer's licence.
"It's great to have a modern-thinking brain and we both have a good deal of input," James said.
"It's lovely to have that young line of thought coming into things and someone to bounce things off.
"It's a true partnership and Robert is also a business partner now and it's all working very well."
Prowess' stablemate Mark Twain will also head to Sydney to contest the Gr.1 Australian Derby (2400m) at Randwick on Saturday week.
The lightly raced son of Shocking finished a gallant fourth in the Gr.1 New Zealand Derby (2400m) at his fifth appearance.
The OTI Racing-owned Mark Twain had broken his maiden at Hawera on Christmas Eve and then beat the older horses over 2100m at Hastings in his lead-up to the Classic at Te Rapa.
After taking plenty of advice, the stable has elected to forego the opportunity of starting the gelding in this Saturday's Gr.2 Tulloch Stakes (2000m) at Rosehill.
"He won't arrive here until next week, we're pretty certain that he's going to make the Derby field so we're not running him this weekend," James said.
"He will have his preparation at home and hopefully we have made the right call."We have spoken with numerous people that have done a lot of homework for us and they have all come up with, at this stage, at least a 90 percent chance of making the Derby without another run and that's our preferred option."