As a player, he was a midfielder, notably in the Premier League with Southampton playing there for over a decade, including their defeat to Arsenal in the 2003 FA Cup Final.

Born in Peterborough, Cambridgeshire,[1] Oakley joined Southampton's youth training scheme, and made his debut at Everton at the age of 17 on 6 May 1995, whilst still a trainee.

[7] Oakley's injury woes began in September 2003 when he suffered damaged knee ligaments in a 1–0 defeat to Middlesbrough, sidelining him for six weeks.

[15] Oakley watched helplessly as an unused substitute as Southampton were relegated from the Premier League on 15 May 2005, after a 2–1 defeat to Manchester United.

[4] Oakley then spent pre-season training with then Premier League team Charlton Athletic, who offered him a one-year deal,[22] and was also chased by Ipswich Town.

[27] However, Oakley admitted that the Derby squad still lacked Premier League experience and felt the need for additional signings.

[28] With Derby bottom of the table by 2008, 10 points from safety, Oakley declared that the team had to beat Bolton Wanderers on 3 January or "the season's over.

[34] Surprised at being allowed to leave Pride Park,[35] he was reunited with Derby teammate Steve Howard, who had joined Leicester ten days earlier.

[3] Oakley was named in the League One PFA Team of the Year together with teammates Jack Hobbs and Matty Fryatt on 26 April 2009.

[48] Oakley formed a fine midfield partnership with Richie Wellens as the club made an impressive start to the 2009–10 season, which saw them seventh in the Championship by September 2009.

[52] He made his 100th competitive game for Leicester in a 1–1 draw against Bristol City on 16 February,[53] and his 100th league appearance in a 2–1 defeat to Reading at the Walkers Stadium on 24 March.

[54] Oakley played a total of 38 league matches to help Leicester qualify for the Championship play-offs,[4] but was not selected for the semi-final legs as Cardiff City won 4–3 on penalties.

[63] On 30 September 2011, Oakley joined League One side Exeter City on loan for a month with the option of extending it until the end of the season.

[66] He made his debut in a 2–0 win over Oldham Athletic on 1 October 2011,[67] drawing praise from manager Paul Tisdale for his performance.

[68] A thigh injury suffered in a 0–0 draw against Carlisle United on 5 November 2011 forced Oakley to return to Leicester after playing seven league games.

[69] Tisdale's concern about "taking somebody back that's injured", coupled with Leicester being unable to confirm Oakley's availability made it unlikely he will rejoin Exeter on loan.

[70] After being released by Leicester Oakley spent the 2012 pre-season training with Exeter City and after much speculation it was announced on 31 July 2012 that he had signed a permanent deal with the Grecians.

[77] After achieving promotion with MK Dons from League Two at the conclusion of the 2018–19 season, Oakley's contract with the club was terminated along with manager Paul Tisdale on 2 November 2019 following a poor run of results.