Bobby O’Leary competed in the men’s 20 kilometres race walk at the 1992 Barcelona Olympic Games, beginning strongly before suffering the consequences of an over-ambitious early pace. He opted to race with the leading bunch from the start and after 5 kilometres was 27 seconds ahead of teammate Jimmy McDonald. As the race progressed in the intense Barcelona heat, fatigue became a factor, his technique unravelled and he was eventually disqualified.

O’Leary was the Irish national record holder in the 20 kilometres race walk at the time of Barcelona.