Strachan began his football career at Coventry City where his father, Gordon Strachan, had taken over as player-manager in 1996. He was loaned out to Dundee in 1998, making nine appearances. Back at Coventry he played in sixteen league games, eleven of them as a substitute; he left soon after the senior Strachan stepped down as manager in late 2001. He scored once during his spell at Coventry; scoring a penalty against Preston North End in the League Cup. In March 2003 Strachan joined Peterborough United, in a loan deal scheduled for the remainder of the season. He joined Southend on a free transfer shortly afterwards however, but was released by the club six weeks later, at the end of 2002/03. He then moved to Hartlepool United on a free transfer. He enjoyed more success here and managed to play regular first team football for three seasons, appearing in seventy-eight matches and scoring seven. During this, the most successful spell of his playing career, Strachan was pencilled into the Scotland international squad, but the call for his first full international cap never came. During the 2005/06 season, Strachan missed a large amount of the season after fracturing a foot against Blackpool. Despite the injury, he managed to complete the match. After recovering, he was loaned out to Stockport County in his third season at Hartlepool. In the 2006/07 season, Strachan saw limited selection by new Pools boss Danny Wilson after the signings of Gary Liddle and Willie Boland. He consequently signed for Peterborough United initially on loan in January 2007, before making the move permanent just two days before the close of the January transfer window. Strachan signed for Notts County on 10 January 2008 after his release from Peterborough United. He scored his first goal for the club in a 2–1 victory against Exeter City on 10 January 2009. On 30 April 2009, Notts County announced that five players would be released from the club at the end of the season, Strachan being among them. He subsequently joined Corby Town F.C. on 24 July 2009. In June 2010 Strachan signed a 1-year deal with Hinckley United Strachan joined United Counties League side St Neots Town in March 2011 scoring on his debut in the UCL cup. St Neots were later investigated as Strachan's registration papers had been delayed.
Coaching career
In July 2011, Strachan returned to Peterborough United as youth team coach, replacing David Oldfield who departed to take up a similar role with West Bromwich Albion. Strachan was subsequently promoted to a first team coach position with Peterborough. In June 2015, Strachan was appointed the new manager of Ilkeston, his first managerial job, after Kevin Wilson left the club to manage National League North side Nuneaton Town. On 16 October 2015, Strachan became assistant manager to Darren Ferguson at Doncaster Rovers. On 26 January 2019, Strachan became assistant manager to Darren Ferguson at Peterborough United after the dismissal of Steve Evans and Paul Raynor. On 22nd June 2020 Strachan became the first team coach at Celtic Football Club.
International career
Strachan received eight caps for the Scotland national under-21 football team, though had no appearances for the senior team. His first call-up was in a friendly against Denmark in March 1998.
Media
In September 2008, Strachan began writing a blog for the BBC News site to help his degree in Professional Sports Writing and Broadcasting at Staffordshire University.