Levein made his name as a defender in Scotland. After two seasons at Cowdenbeath, he spent the next 14 years at Heart of Midlothian and was the Scottish PFA Young player of the Year in 1985 and 1986.
Despite two serious knee injuries, he made over 450 appearances for the Tynecastle club, many as captain. During his playing career there, Hearts finished runners-up in the Scottish Premiership, as well as reaching the 1986 Scottish FA Cup final.
Levein also played for Scotland 16 times between 1990 and 1994, including an appearance in the 1990 World Cup finals in Italy.
Forced to retire in 1997 with another knee injury, he managed Cowdenbeath between 1997 and December 2000, laying the foundations for their promotion in May 2001, by which time he had returned to Heart of Midlothian as manager.
In October 2004, Leicester City, struggling in the Championship following their relegation from the Premier League, appointed Levein as their new manager, with Rob Kelly as his assistant.
The board was impressed by his achievement in rejuvenating Hearts and in leading them into Europe for two successive seasons.
With Leicester City’s period in administration a recent memory, Levein's vision was to develop players through the Academy, reduce the age of the squad, sign younger players on long term contracts, have players living locally, and ensure financial prudence.
He soon signed Alan Maybury, Mark de Vreis and, later, Patrick Kisnorbo from his old club, but by New Year 2005, the team was struggling in 15th position in the Championship.
However, Leicester did reach the quarter-finals of the FA Cup, before succumbing to Premier League Blackburn Rovers.
The 2005/06 season started badly with a 4-1 defeat at Sheffield United. David Connelly, meanwhile, was transferred to Wigan Athletic on the August transfer deadline day, just after 15 year-old Ashley Chambers had become the Club’s youngest-ever player.
Six successive league defeats between mid-December and the end of January left Leicester City in 22nd-place in the Championship table, although amazingly, after the third of these defeats, Tottenham Hotspur were defeated 3-2 in the FA Cup after they had taken a two goal lead.
Despite the signing of Matty Fryatt, in late January, Levein was sacked following the sixth defeat in succession at Plymouth. Kelly, his assistant, was appointed caretaker manager, assisted by Mike Stowell, and the Club was able to stave off relegation.
After a brief period managing Raith Rovers, Levein became Dundee United’s manager in October 2006, additionally becoming, director of football in 2008.
Levein left Tannadice Park in December 2009 for a three-year spell as Scotland’s national team manager, but failure to qualify for the 2012 UEFA Euros and a lack of success in qualifying games for the 2014 FIFA World Cup resulted in him leaving the post in November 2012.
Eighteen months later, Levein returned to Hearts as director of football, together with the post of manager, to which he was appointed in August 2017.
He departed the manager's position on 31 October 2019, although he was retained in an advisory role for the rest of his contract.