Damien Oliver commenced his riding career in Western Australia in 1988 where he rode 66 winners on metropolitan and provincial tracks and was leading apprentice for the 1988/89 season. He then accepted an invitation to come to Melbourne for a three month trial period with trainer Lee Freedman – and remained indefinitely. Under Freedman, Oliver had a stellar apprenticeship, riding 478 winners.

His first Group 1 came with Submariner for Bart Cummings in the Show Day Cup in 1990. By the end of his apprenticeship in 1993, he had a record 18 Group 1s to his credit, including the Caulfield Cup on Mannerism. He won the Victorian Jockeys' Premiership twice as an apprentice.

During the next decade Oliver established himself at the very peak of his profession. He added five more Victorian Jockeys' Premierships to his tally, and won the Melbourne Cup three times, the Caulfield Cup four times, and the Cox Plate twice. He has been awarded the Scobie Breasley Medal for Victoria's leading rider six times. His winning ride on Fiorente in the 2013 Melbourne Cup brought his Group 1 tally to 98.

Oliver has also ridden overseas with distinction, particularly in Hong Kong.

Oliver was inducted into the Hall of Fame in 2008.

Image Source: Australian Racing Museum Collection