The race was run between what were then Australia's two largest shopping centres: Westfield Parramatta, in Sydney, and Westfield Doncaster, in Melbourne. He ran at a slow loping pace and trailed the leaders for most of the course, but by denying himself sleep and running while the others slept, he slowly gained on them and eventually won by a large margin.
Before running the race, he told the press that he had previously run for two to three days straight rounding up sheep. He claimed afterwards that during the race, he imagined that he was running after sheep and trying to outrun a storm.
The Westfield run took him five days, 15 hours and four minutes, trimming almost two days off the record for any previous run between Sydney and Melbourne. All of the six competitors who finished the race broke the previous record, but Young beat them by running while they were sleeping.
In 1997 at age 76, he made an attempt to beat Ron Grant's around Australia record and completed 6,520 kilometres of the 16,000-kilometre run, but he had to pull out because his only crew member became ill.In 2000 he achieved a world age record in a six-day race in Victoria.
Renowned for his then ungainly running style, Young ran more than 20,000 kilometres during his competitive career.
The "Young shuffle" has been adopted by some ultra-marathon runners because it expends less energy. At least three winners of the Sydney to Melbourne race have been known to use the "Young shuffle" to win the race. In 2010, comedienne Hannah Gadsby named her Sydney Comedy Festivalshow "The Cliff Young Shuffle" in tribute.