Oakley first played for Thornbury RFC, and attended
Marlwood School where he played for the school's team. Oakley played for North Bristol RFC and
Clifton RFC, before joining the
Bristol U21 side, and ultimately gaining a first team contract. Oakley played in the Premiership for
Bristol Shoguns, where he made 19 starts for the club. He was named as man of the match on his second appearance, a
Heineken Cup match against Clermont. At the end of the 2005–06 season, Oakley and teammate
Leigh Hinton were released by Newport Gwent Dragons, and joined
Leeds Tykes on a two-year deal, for the start of the
National Division One 2006–07 season, making his debut against
London Welsh at
Headingley on 3 September 2006. Following Leeds' relegation at the end of the
2010–11 Premiership season, Oakley used a release clause to exit his contract with the club, and joined French club
CS Bourgoin-Jallieu. Oakley spent one season with the side, before returning to the Premiership with
Northampton Saints. Oakley played for the Saints for one season, and joined
RFU Championship team
Plymouth Albion R.F.C. as a player-coach in 2013. In 2015, Oakley suffered a leg fracture while playing for Plymouth, ending his season and coinciding with the club's relegation from the Championship. Oakley departed Plymouth Albion in 2015, and joined
Hartpury University R.F.C., again as a dual player-coach. While with Hartpury, Oakley was appointed as team captain, and helped the club gain promotion from National League One to the Championship. In 2018, Oakley was diagnosed with cancer, putting his playing career on hold. He successfully recovered, but retired from playing, remaining active as a coach. == International career ==