O'Leary (15) was the dominant sculler, winning six races, and Winders (17) won five.
O'Leary was inspired by the efforts of her brother, Jack, who was a key member of the New Zealand quadruple sculls crew that won the silver medal at the world junior championships in Lithuania this year.
''I watched the race live on my computer,'' Anna O'Leary said.
''Jack's performance has given me a lot of inspiration.''
Winders has been encouraged in the sport by her mother, Christine, a former New Zealand lightweight champion.
''Mum is relaxed and doesn't push me. But she gives me a few tips and a lot of encouragement,'' Winders said.
The performances by the pair were not enough to help their club, Otago, topple the strong North End club, which retained the Butterfield Shield with 93 points to Otago's 88.
But the gap between the clubs has closed. Last year, North End won by 21 points.
The top two clubs were followed by Columba College 16, University 12, Port United 10 and Queen's High School 5.
O'Leary was a convincing winner of the club single sculls from Emma Wallace (North End).
But her most significant wins were in the open women's events. She and Winders won the double sculls, from the Otago University combination of Nicola Shanks and Caitlin Buist, and were joined by Hannah Duggan and Rebecca Pitcaithly for a convincing win over Otago University in the women's quadruple sculls.
Winders won the under-18 double sculls with Pitcaithly, and won her division of the club single sculls.
Jack O'Leary was the dominant male sculler and comfortably won the men's open single sculls when Matt Smaill (University) fell out of his boat.
He won two other events, the most significant being the open four with Alex Yarnall, Daniel Hobson and Tom Grave.
North End won the regatta because of its dominance in the sweep oar events and especially its wins in four of the five eights races.
Claudia Maker stroked crews that won the women's under-15 and the open women's eight. She also won the women's under-15 double sculls with Josie Cook.
Her father, Kelvin Maker, was not so lucky because he was disqualified for cutting across another boat's lane in the masters men's single sculls.
That race was won by clubmate Dave Hanan. The pair teamed up to win the men's open pair from the University combination of Matt Smaill and Tako Sako.
Port United dominated the women's masters events with the quadruple sculls of Imogen Coxhead, Robyn Cameron, Allison Howlett and Michelle Johnson beating North End. Coxhead and Cameron beat Howlett and Johnson in the double sculls.
