"I had nothing to lose and put the hammer down and he responded," he said, opting for the express ride to alight with four faults in 42.24s.
Watching from the horse-shoe entrance, he and Wilson exchanged high-fives on their horses as they watched Olympian Laurie (nee McVean), of Mystery Creek, drop a rail to release the pressure valve on the pair.
"Vicki is a very fast rider so to better her time is quite cool," he said after Wilson set the benchmark on four faults in 44.21s.
The family bred Dollar Rolls out of Dollar Belapierre at Matawhio Sport Horses where three generations have persevered for more than a decade. Willis had competed on the horse's mother, Capriole, in the young rider class.
"She won quite a few classes and was very well performed there."
Willis revealed the family had big hopes on Dollar Roll MS' sister but she injured her fetlock and never came right.
He started competing at the maiden HOY Show in Hastings but had a hiatus when he rode professionally in Europe before returning home a couple of years ago.
Having never won a class here before, he put it down to having some luck go his way yesterday.
"You've got to have a good horse and have everything go right."
Without doubt Willis is partial to German designer Werner Deeg's "nice and flowing" course where "the questions aren't too crazy ..."
He dedicated his maiden bling at top level to his mother, Mary-Beth Sharp, who bred Dollar Rolls.
"The amount of time and effort she has spent on the horses and me previously, and the breeding programmes set up in Auckland ... it's great to see it all come to fruition," he said, withdrawing Dollar Rolls from the Silver Fern Stakes tomorrow night to focus on the Olympic Cup on Sunday.
DAY 2 RESULTS
■ Virbac Equine Norwood Gold Cup: William Willis (Karaka) Dollar Roll MS 1, Vicki Wilson (Hikurangi) Caretino Jewel 2, Katie Laurie (Mystery Creek) Dunstan On The Point Sandy 3, Rose Alfeld (Leeston) My Super Nova 4, Emily Hayward-Morgan (Te Awamutu) AP Ninja 5, Katie Laurie (Mystery Creek) Dunstan On The Point Eve 6.
■ AHD Ltd 6-year-old of the year (part of the Mitavite Breeding Series): Mathew Irvine (Takapau) La Perla 1, Kirsten Worker (Auckland) Melanie's Choice 2, Duncan McFarlane (Taupo) Be Mine NZPH 3, Tegan Fitzsimon (Canterbury) Windermere Cappuccino 4, Vicki Wilson (Hikurangi) LC Showtym Cassinii 5, Julie Davey (Hastings) JD Ruby 6.
■ GJ Gardner Homes pro-amateur rider of the year (part of the Let's Bale pro-amateur series): Emma Gaze (Ohaupo) Fire Bug 1, Bob Bleakley (Cambridge) Airthrey Resolution 2, Rosie Commons (Auckland) Athena GNZ 3, Tim Pearce (Marton) Oracle WT 4, Louise Bowie (Pahiatua) Kiwi Hammer 5, Kelly Smith (Foxton) Corlinka 6.