Oliver announced his arrival at four star level with an impressive Badminton debut in May 2005, completing a clear round cross country within the time to finish in 12th place with Topping. As a result he had his first taste of international competition when he was named as one of the riders to represent Great Britain as an individual at the European Championships at Blenheim in September 2005.

In 2006, Oliver bettered his Badminton record with new ride Flint Curtis for third place and subsequent selection for the World Championships in Pratoni where the pair won team gold medal in 2007.

Yorkshire born and bred, Oliver inherited his love of horses from his parents. His mother Eve showed side-saddle at county level and his father Alan competed successfully in three day eventing, including at Burghley Horse Trials.

Oliver’s early success was gained on 14.2hh pony Cool Mule, with whom he won a class at the Horse of the Year Show and represented GB on the Pony Eventing Team at the European Championships.

As a teenager he produced Gold Ringer to Grand Prix level show jumping and advanced eventing, and won a show jumping Home International Young Rider gold medal with Kilkenny Diamond.

Oliver moved south and spent three years as stable jockey to British Team Trainer, Kenneth Clawson before setting up his own yard just outside Market Harborough, before moving to his current base in Shropshire. Oliver has an impressive string of horses and there are few competition days when he is not in action.

Fiercely competitive, he has earned a reputation for getting results with difficult horses, including his Badminton ride Topping. He is backed by Toggi and has also benefited from being on the World Class Potential squad.

In 2008 he won the inaugural Express Eventing competition with Flint Curtis and bagged £100,000 in prize money. The combination also won the 60th anniversary Badminton competition in 2009 and also Burghley 2009.

2010 saw Oliver experience a horrendous fall at the Rolex Kentucky. Photographs appear to show Ashdale Cruise Master fall onto Oliver's face at fence 20 of the cross country course, incurring cracks to his collarbone, sternum and ribs. The fall cost him the chance to win grand slam, having already won Badminton and Burghley, but he was back in the saddle and the combination won at Tattersalls five weeks later/ He also won the Novice Championships at Gatcombe with Jeepers Creepers, a horse to watch out for in the future.

2010 also saw the return of the Champions Tour with Geoff Billington.