Obree was born in Nuneaton, a large town in northern Warwickshire, England, but has lived almost all his life in Scotland and considers himself Scottish. An individual time triallist, his first race was a 10-mile time trial to which he turned up wearing shorts, anorak and Doc Marten boots. He thought the start and finish were at the same place and stopped where he had started, 100 metres short of the end. He had started to change his clothes when officials told him to continue. He still finished in "about 30 minutes."