Midfielder Matt Oakley played over three hundred times for Southampton, and had enjoyed significant spells with both Derby and Leicester, when he embarked on a lengthy association with Exeter City in 2011.  Making around 170 first-team appearances - and becoming City's oldest-ever EFL player in the process - Matt had become assistant manager by the time of his departure in 2018.

Having joined Southampton as a trainee in 1993, Matt made his first-team debut as an 18- year-old against Liverpool in December 1995. Becoming a regular in the Saints side from 1996/97 onwards Matt represented England at under-21 level and was a member of the Southampton team which lost to Arsenal in the 2003 FA Cup final. Then, after amassing 311 appearances (20 goals) in all competitions for the South Coast club,  Matt moved to Derby County in August 2006 where he played 63 league and cup games scoring nine goals in the process. Thereafter Matt joined Leicester City in January 2008 for whom he appeared in 148 competitive fixtures ten contributing goals.

After playing in two League Cup ties early in 2011/12 Matt, at the age of thirty-four, found himself joining a club on loan for the first time in his career when he arrived at St James’ Park in September 2011. Making his first appearance against Oldham Athletic on 1 October 2011, a thigh injury cut his initial Grecians stint to just seven games including the 4-4 draw at Sheffield United.     

With the Grecians now back in League Two, and Matt having been released by the Foxes, he agreed a permanent deal with City in July 2012. Reappearing against Morecambe on 18 August 2012, Matt had appeared in 37 league and cup matches when a shoulder injury prematurely finished his season in mid-March. 

Returning against AFC Wimbledon in August 2013, Matt played 24 times in his second full season with the club followed by 48 competitive appearances in 2014/15 and another 33 in all competitions in 2015/16. Then, gradually taking on more of a coaching role, Matt made 23 appearances during his final playing season ahead of his last professional game - the 694th of his career - against Barnet on Good Friday 2017 by which time he was City's oldest-ever EFL player at the age of 39 years, 7 months and 28 days.

Becoming full-time assistant manager ahead of the 2017/18 season, Matt spent a final season at St James’ Park before following Paul Tisdale to Milton Keynes Dons in 2018. In time, after winning promotion at the first attempt, he was to leave the Buckinghamshire club within six months of that success when he was sacked alongside Paul Tisdale and first-team coach Danny Butterfield in November 2019.

Thereafter Matt worked in the world of sports agencies and football consultancies with both the 366 Group and Modus Operandi Sports.