His father, Ray Oliver, was a jockey who died in Kalgoorlie from falling off his horse when Damien was three years old.

[5] Oliver's riding career started in 1988, and he completed his apprenticeship with his stepfather Lindsey Rudland and Lee Freedman.

Unfortunately he suffered a series of injuries including a broken spine in March 2005, sustained in a fall at Moonee Valley.

[6] He returned to riding after that back injury and rode the Japanese horse Pop Rock in the 2006 Melbourne Cup, which finished second to stablemate Delta Blues.

Oliver has won the Melbourne Cup three times: on Doriemus (1995), Media Puzzle (2002),[8] and Fiorente (2013);[9] the Caulfield Cup on Mannerism (1992),[10] Paris Lane (1994), Doriemus (1995), and Sky Heights (1999); the Cox Plate on Dane Ripper (1997) and Northerly (2001); and the Blue Diamond Stakes on Alinghi (2004).

On 22 September 2010, Oliver pulled out of rides at a Sandown meeting, while helping police with their inquiries into a criminal investigation.

His final ride and win on Munhamek was in a race named after him, the Damien Oliver Gold Rush over 1400m.

Europa Point finished sixth but stewards had no issue with the way Oliver rode his horse, saying there was no change from the usual racing pattern or any other reason to doubt the integrity of the ride.

[20][22] Damien Oliver has won Racing Victoria's Scobie Breasley Medal fourteen times (1996, 1999, 2001, 2002, 2003, 2004, 2005, 2010, 2013, 2014, 2015, 2018, 2019 and 2020).

[22] Oliver's elder brother Jason was also a jockey; he died on 29 October 2002 after a fall at Belmont Park Racecourse, Western Australia, when a young horse he was riding broke both front legs and fell during a race trial.