President Daniel Irvine said the scholarships were reinstated in a bid to encourage more young people to join the oldest aero club in New Zealand, which was founded in 1927 and boasts about 200 members.
"The aero club's guiding principle has been fostering aviation in Otago," he said.
The scholarships, one for a male and one for a female, attracted 16 "very eager applicants" who completed practical tests and interviews.
"A large part of the scholarship is attitude."
However, the judges had a hard time selecting just two budding pilots, so also awarded subsidised flying lessons to Campbell Angland and Corban Phillips.
Henry was "pretty excited" to be chosen and hoped the opportunity would lead to a career as a commercial pilot.
He had two flying lessons about a year ago, but the scholarship announcement encouraged him to get reinvolved in the activity he has been fascinated with since childhood.
Annalese also hoped to forge a career in aviation, and possibly the air force.
Her father used to fly helicopters, and while she had never flown before she was keen to learn.
"I can't even describe it. I can't believe it," she said of winning the scholarship.