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O'Shea (23), an accountancy student at the University of Otago, won the 22nd annual Time Buster in 32.70sec and was followed home by clubmate Robert Jopp (34sec) and Taieri's Blair Grant (34.53sec).
The 243m street race starts and finishes outside the New Zealand Shop when the Town Hall clock strikes the first of its 10 strokes at 10am.
O'Shea, cheered on by a large crowd from a visiting cruise ship, came close but failed to reach the finish before the clock struck 10.
He was feeling the pressure as he came up the slope to the finish.
''I kept trying to drive the arms and keep good form,'' O'Shea said.
It was the first time O'Shea had competed in the race and he did not know what to expect at the start.
The key to the race is to be the first runner to the top of the hill by Robbie Burns statue. O'Shea held the inside and just edged ahead of last year's champion Jopp at the top of the hill.
Jopp knew how important it was to be at the top of the hill first and applied extra pressure but could not get in front of O'Shea.
''It was tough going up that hill,'' O'Shea said.
''I hadn't done it before and didn't know what to expect.''
Jopp (17), a pupil at John McGlashan College, has had hamstring problems this season and did not want to push that extra bit to get in front.
''It was tight at the top,'' Jopp said.
''Daniel's a 400m runner and I knew he would have it at the end. If I was to win I knew I had to do it at the start.''
O'Shea made his break on the field on the downhill stretch to the Regent Theatre.
''I was able to float down the hill and it made it a bit easier,'' he said.
''But there were sharp corners and that made it hard on the body.''
O'Shea was just 2m short of the target when the clock struck 10 and failed to add the bonus of $250 to his winner's purse of $300.
Grant (18), who finished second last year, ran a solid race for third.
The surprise packet was Chris McNoe (Hill City-University) who was close behind Grant and finished fourth in his first attempt at the race. His time was 34.95sec.
Fiona Hely (Hill City-University), who won the race four years ago, gained her second win in the women's event in 38.43sec.
Hely (24), who works in mathematical modelling, was always in command of the women's race and led from the start.
She won going away by 1.43sec from Zoey Flockton (Taieri) 39.86sec and Brigid O'Neill (Hill City-University) 41.21sec. It was a strong run by Flockton (17), a pupil at Columba College, who finished fourth last year.