Leicester's League 1 Title-Winning Captain – Oakley's Spell As Foxes Skipper
Peterborough-born midfielder Oakley spent over a decade as a star player for Southampton, mainly in the Premier League, as he emerged through the academy to become recognised as a top-flight player.
While still a trainee for the South Coast club, Oakley made his senior debut for the Saints at the age of just 17 against Everton in May 1995, but it was in the 1996/97 season that he truly emerged.
Initially breaking through at St. Mary's Stadium under the management of Graeme Souness, Oakley's performances for Southampton allowed them to become a steady, mid-table Premier League side.
At the end of the 2002/03 campaign, meanwhile, he was instrumental to the club's bid for FA Cup glory, but Oakley and his team-mates were defeated by Arsenal in the final at Millennium Stadium, Cardiff.
Oakley's injury problems midway through the new decade, though, coincided with a decline in the Saints' form and he watched on helplessly as Harry Redknapp's men were relegated in 2005.
He recovered from his injury to star 29 times for the club, now managed by George Burley, in the Championship, but after 311 Southampton appearances, he signed for Derby County in August 2006.
While Michael Johnson was club captain at Pride Park, Oakley was swiftly made team skipper for a 2006/07 season which would end with Billy Davies securing promotion via the play-offs.
Back in the Premier League, Derby struggled to acclimatise to the higher level and, by early January, Oakley declared a clash with Bolton Wanderers as a 'must-win' game. The Rams lost out 1-0.
Feeling Derby were set for relegation, which did eventually occur, Oakley was approached by Foxes manager Ian Holloway, who was looking to rescue the Club from its first-ever relegation to League 1.
A reported fee in the region of £500,000 was agreed between the two East Midlands rivals and Oakley followed Steve Howard - another integral member of Derby's promotion-winning side, to Walkers Stadium.
Despite considerable investment by Leicester during the 2007/08 season, the Foxes simply couldn't find a winning formula and Holloway, appointed before Christmas, was the third full-time manager of the season.
Oakley's debut for the Club arrived on 12 January, 2008 as fellow new recruits Howard and Barry Hayles netted in a 2-0 success over Coventry City, which gave the Blue Army false hope of a reversal in form.
While Oakley and Howard were undoubtedly assured signings, Leicester's problems ran too deep as they approached the end of the season under the very real threat of dropping into the third tier.
A dramatic 3-1 defeat by Sheffield Wednesday on Filbert Way, including an Iain Hume missed penalty which would have levelled it at 2-2, left City in a precarious position as they travelled to Stoke City on the final day.
Their chances were hit further by the fact that Stoke were fighting for promotion and a 0-0 draw in Staffordshire ended up being enough for the Potters, but not for the Foxes, who dropped down into League 1.
Holloway was replaced in the summer by Nigel Pearson, the man who had guided Southampton to safety at Leicester's expense, in what turned out to be a real turning point in the Club's fortunes.
Oakley was made captain in League 1 as the Foxes stormed to an instant return to the Championship, securing 27 league victories and 96 points, as Pearson's men lifted the title in style.
City's No.8, on the other hand, starred on 45 occasions in the league for City and led his team-mates with distinction, but both Oakley and the rest of the Leicester squad had their eyes on further success.
Despite many considering the 2009/10 season to be one of consolidation for Leicester, back in the Championship, Pearson's men were quietly confident that they'd be able to challenge for successive promotions.
In came Richie Wellens, Paul Gallagher and Dany N'Guessan, but despite a healthy contingent of midfielders, including Andy King, Oakley remained in Pearson's plans, occasionally in an unfamiliar right-sided berth.
Oakley, now in his early 30s, was a reliable presence in the team and he made a further 38 outings for the Foxes, who finished fifth, before injury curtailed his season, just as a bid to win the play-offs began.
He was forced to watch on as his colleagues tackled Cardiff City in a two-legged semi-final, losing out to a brilliant Peter Whittingham free-kick in the first clash at King Power Stadium.
However, City were exceptional in the Welsh capital, eventually winning out in normal time 3-2, thanks to goals from Matty Fryatt, a Mark Hudson own goal and Andy King's second-half header.
That was enough to take the tie into extra-time, but when penalties came, it would turn into an evening to forget for City, who had performed so superbly all night at Cardiff City Stadium.
Missed spot-kicks from Yann Kermorgant and Martyn Waghorn were punished by the Bluebirds and the Foxes were denied a chance to tackle Holloway's Blackpool in the play-off final at Wembley.
A period of considerable change then occurred at Filbert Way as Pearson departed to join Hull City before Paulo Sousa and then Sven-Göran Eriksson took charge of Leicester during the 2010/11 season.
Despite several managerial changes, including Pearson's return to the Club in late 2011, Oakley remained a prominent member of the first team, leading to a total of 148 appearances - and 10 goals - for the Club.
Naturally, as Oakley got older and investment into the first team began to pick up under King Power's ownership, his appearances began to become limited, but his experience was a useful tool off the pitch.
In 2011, the former Southampton midfielder departed the Club on a short-term loan deal, electing to join League 1 side Exeter City, despite speculation of a return to Derby.
Oakley's ability and know-how made him a vital member of Paul Tisdale's side in the third tier, however another injury would eventually cut the loan spell short.
He did, though, eventually join Exeter full-time, adding another five seasons to his 23-year career, before ultimately retiring in 2017 and rejoining Tisdale as assistant manager at MK Dons a year later.
Oakley, though, remains a player associated with the very beginnings of Leicester City's greatest-ever era, laying the foundations for their incredible rise from League 1 to lifting the Premier League title in 2016.
He also remains one of just 12 Foxes captains past and present to have lifted a trophy in the Club's colours and his committed performances for Leicester are still remembered fondly by the Blue Army.