McIndoe began his career at Luton Town, where he made his home league professional debut at 18 years old against Burnley on 5 September 1998.

While playing for Doncaster Rovers he set a record scoring ten penalties which was more than any player in the English Football League in the 2005/06 season.

[7] Former teammate Matthew Upson[7] also played a huge part in advising McIndoe who would now focus on being the best athlete he could be and has been teetotal ever since.

His performances quickly put him on the radar of other Conference teams where a bidding war began between Boston United and Yeovil Town for McIndoe's signature.

[17] In the following 2002–03 season McIndoe made more appearances than any other player and was a key component in making club history, when Yeovil were crowned champions of the Nationwide Conference for the first time in 107 years.

McIndoe opened the scoring in the fourth minute, beating goalkeeper Manuel Almunia from a tight angle.

In March 2006, Championship side Derby County moved in to sign McIndoe on a loan deal until the end of the season.

For the second season running he finished as Rovers' top scorer with 13 goals (10 from penalty kicks), and was voted into the PFA Team of the Year for League One.

Derby County manager Terry Westley brought McIndoe in on loan in March 2006, as he tried to try to help keep the club in the Championship.

On a 22 April 2007 Wolves played Birmingham City in the West Midlands derby, McIndoe scored two headers but then missed a penalty in the last minute for a hat-trick, losing 3–2.

In July 2007, McIndoe signed a three-year contract with Championship club Bristol City[46] reuniting with manager Gary Johnson[47] for an undisclosed fee believed to be in the region of £500,000.

On 4 August 2009, Championship club Coventry City signed McIndoe on a 2-year contract under manager Chris Coleman for an undisclosed fee believed to be around £325,000.

[51] He received his third international call up against Japan in Yokohama, but the winger pulled out of the squad due to a minor knee injury.

In 2010–11 McIndoe signed a short-term loan deal with the League One side Milton Keynes Dons to maintain his match fitness before returning to Coventry City in the Championship.

[54][55] Newly appointed caretaker manager Andy Thorn put McIndoe straight back into the squad for the majority of the remaining matches in the 2010–11 season,[56] where he played a part in helping Coventry City retain their Championship status.

In the 2013–14 season McIndoe along with old Luton Town and MK Dons teammate Jude Stirling helped to coach young players at London Elite while playing alongside them.

[60][61] He signed a short-term deal as a favour to manager Kieran McAnespie and coach Marc McCulloch, in return gaining match fitness preparing him to go back into the professional game.

After being given the caretaker manager role,[66] in his first match, he led Gretna 2008 in a 3–1 win against Edinburgh University in the first round of the Scottish Cup.

[72] The chairman John Dickson publicly apologised to McIndoe and his coaching staff for putting them in this position, commending his character and commitment to the club.

His tactical leadership and the team's cohesion were key to their success, including outstanding contributions from forward Connor Young.

Young was simultaneously awarded SPFL League Two Player of the Month for his goal scoring performances, further showcasing the effectiveness of McIndoe's management.

[74] For the second time in the 2024/25 season, McIndoe was awarded SPFL League Two Manager of the Month for December 2024 after some impressive performances and results.

[58][77] It is a detailed account of his upbringing on the Calders Estate in Edinburgh, his professional football career and his nightclub on Oxford Street in London.