Each swimmer's leading three efforts count towards the series, with double points on offer at the final race in April, the State King of the Bays. That makes it the most important of the series with $20,000 up for grabs for series winners.
"If I can pick up one more win, it'll all come down to the King of The Bays. It's going to be an interesting series."
In the women's race, Taranaki's Webby surprisingly dominated rival Cara Baker.
After swimming together at the start, Webby moved into overdrive at the 1000m mark and won by just over a minute.
Her victory was a big boost for her, after disappointing efforts at the NZ Championships two weeks ago, which Baker dominated.
"I was lacking confidence before going out, because my last two ocean-water swims haven't been great. So I was hoping to have a good race, and I'm really happy about it," Webby said.
The women's series is now nicely set up. Webby has won two of the three races, and Baker one.
Overhead conditions for the 3.3km races were glorious in Wellington, the water though was slightly choppy.
The next race in the series is the State La Grande Classic in Akaroa, February 23.