Askey worked at Macclesfield Town as reserve-team manager, leading the reserves to the Football Combination Division Two title. He went on to work as assistant manager to David Moss before taking over as caretaker manager on 27 October 2003 when Moss was dismissed with the club in 20th place in the Third Division. He was appointed permanently in December after winning three of his seven matches in caretaker charge. Askey was demoted to assistant manager to new manager Brian Horton on 1 April 2004 with Macclesfield second from bottom of the Third Division. Horton managed to steer the club out of the Third Division relegation zone. Askey stayed on as assistant manager, and with the arrival of Paul Ince moved on to work as youth-team manager.
