Cleland was assistant manager to Steve Morrison at East Stirlingshire before joining Partick Thistle in January 2004.
[4] On 21 June 2004, Cleland was appointed as youth coach at Livingston, taking over from Paul Hegarty who left to join Dunfermline Athletic.
[7] Then following the sacking of John Robertson in April 2007[8] which ultimately led to him leaving the club a month later when he failed to become permanent manager.
Following their relegation, Cleland was released as a coach by Inverness Caledonian Thistle to cut costs but shortly afterwards took up a similar position at St Johnstone.
[12] He was again put in caretaker charge of St Johnstone in May 2020, after the resignation of Tommy Wright,[13][14] and October 2023, after Steven MacLean was sacked.