Leven was a youth player with Rangers and as a 16-year-old appeared on the bench four times for the first team, including an Old Firm match.
As Aaron Downes made a poor start to the 2007–08 season, Leven was given the captaincy of League Two side Chesterfield.
[4] There was interest in Leven from several clubs, including Millwall[5] and Crystal Palace,[citation needed] but in July 2011 he signed a two-year deal with League Two side Oxford United.
Leven set up both Oxford United goals in their 2–1 away win over arch-rivals Swindon on 21 August 2011, their first victory at the County Ground for 38 years.
[8] While a free agent, Leven was linked with Paul Ince's Blackpool, but in August 2014 he signed for non-league Jarrow Roofing BCA.
[21] After a good run of results and a 3-3 (6-5 on pens) loss to Celtic in the Scottish Cup, Leven stepped back as Caretaker for the arrival of permanent appointment Jimmy Thelin.