He would initially remain with Darlington following the end of his playing career and worked in a variety of roles at the club, as well as managing the first team on a temporary basis on three occasions.
Maddison signed as a trainee with Southampton in 1984 and stayed with them until 1997 when he made a £250,000 transfer to Middlesbrough where he spent time on loan to Bansley and Bristol City (where he scored once against Oldham Athletic).
On 30 September 2006, David Hodgson was suspended by the club following a run of poor results and a possible approach from AFC Bournemouth, leaving Maddison and Martin Gray as joint caretakers for up to two weeks while an internal investigation was carried out.
On 8 May 2009, it was reported that Darlington's administrators, Brackenbury Clark and Company, had released the majority of the first team squad from their contracts to cut costs, with immediate effect, as well as the club's coaching staff and administrative staff including the caretaker manager Martin Gray, leaving Liddle and Maddison as joint temporary caretaker managers.
[8] On 21 March 2010, Maddison joined Liddle as caretaker yet again after the sacking of Staunton,[9] before Simon Davey was appointed manager on 1 April.