The Sunshine regatta will create some history of its own as the first time the titles have ever been held outside of Sydney.
The event will also mark the inaugural Lake Macquarie Historic 10-Foot Skiff Championship.
Gillespie and his crew of two others won last year with a handicap of 10 minutes, which is deducted from the overall time to form the handicap placing.
But that benefit has been cut to five minutes this year, so Gillespie tips past winner John Lewis's entry "Keriki" (off 10 minutes) to claim handicap honours.
"If we were a racehorse we'd probably be carrying too much weight," he said.
South Lakes club stalwart Pete "Alfie" Jacobson has built a boat, "Miss Marlene".
His son Dale Jacobson, along with Dale's wife Tracey and Alfie's son-in-law John Hodda, will race it in the titles, which will end with two races next weekend at Drummoyne.
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