Career
Cleland started his career with Dundee United, for whom he made 159 appearances, lifting the Scottish Cup in 1994. He signed for Rangers in a joint deal with Gary Bollan in 1995 and established himself in the right-back slot at Ibrox. After over 100 appearances for the Glasgow club, he joined Premier League side Everton along with manager Walter Smith in 1998.
However, his time in England was blighted with constant injury problems, and he only made 44 appearances before retiring in 2002.
Cleland was the youth coach of Livingston until May 2007. He also took on a caretaker-manager role on three occasions, the most recent being after the resignation of Paul Lambert on 11 February 2006.
He was also assistant to Steve Morrison (football player) at East Stirlingshire. Cleland was appointed as a youth coach at Inverness Caledonian Thistle in January 2008.
Following their releagation, Cleland was released as a coach by Inverness Caledonian Thistle to cut costs but shortly afterwards took up a similar position at Street Johnstone.
Cleland was made caretaker manager of Street Johnstone in October 2011, when Derek McInnes and Tony Docherty moved to Bristol City. Before being appointed as a youth coach at Livingston F.C. Cleland had a brief time at Rangers F.C." Murray park coaching youths in a programme set up by Rangers to help scout young talents.