Liam Dixon missed the finish line in his only other Sparke Helmore Triathlon appearance.
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But the Maitland 18-year-old did not put a foot wrong on Sunday as he sprinted to victory with a blistering run leg.
Dixon was neck and neck with Pelican 44-year-old Nathan Stewart, a multiple event winner, and Belmont 24-year-old Hamish Longmuir, who was the defending champion and now races professionally, as they entered transition from the bike to run.
But he quickly opened up a lead and crossed the finish line at Newcastle Foreshore in 57 minutes and 33 seconds.
Longmuir, who races on the 70.3 triathlon series, was second in 58.14 and Merewether's Ben Maunder, 30 and a relative newcomer to the sport, placed third in one hour and 10 seconds.
Stewart carried an injury into the race and limped through the run leg to finish sixth in 1:02.19.
"This is the second time doing this event," Dixon said post-race.
"I did the enticer in 2018 and came third but I missed the finish line. I ran past it and had to run around the back and jump the fence.
"I raced last weekend but I've had a bit of an easier week. I felt pretty good in the swim and was just hoping to swim and bike with everyone and then just let my running do the rest in the end."
Dudley 42-year-old Regina Jensen, who claimed the Australian marathon crown in Sydney in September, collected her sixth Sparke Helmore Triathlon win but her first in over a decade.
Jensen raced professionally but retired from triathlon before having her two children - Harry, 11, and Emily, eight.
She finished the course of 750-metre swim, 21-kilometre cycle and 5km run in 1:07.47.
Dungog teenager Emily Fortunosa-Klocker (1:09.28) was second after being first off the bike, and New Lambton's Courtney Wevers (1:11.49) placed third.
Jensen has been racing in the Sparke Helmore Triathlon for almost two decades. It has traditionally been held in February but was rescheduled to November this year due to a clash with Supercars set-up.
"I retired from triathlon when I was pregnant with my son, so it's 11 years," Jensen said.
"I've done the odd one because I do love it but my swimming training these days is water polo and nippers."
Jensen concentrates mostly on running these days but enjoys returning to her roots for events like the Sparke Helmore Triathlon.
"I want to keep those young girls honest," Jensen said. "It just reminds them that they've got to work for it.
"I'm so grateful for everything triathlon has given me. It was this race where I first understood I had a bit of talent in sport and then one opportunity rolled into another rolled into another, and I'm just so grateful for everything it's given me and everywhere it's taken me.
"Even when I raced professionally, I still liked to come back to home events, grassroots stuff."
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