After the spell at Notts County, Hart was appointed manager of Chesterfield in 1988. Joining the club when they were firmly rooted to the bottom of the Third Division, he reorganised and revitalised the playing side of the club with assistant Chris McMenemy. Thanks especially to a number of notable number of home wins in the first three months of 1989 and a surprising 3–1 win at second place Sheffield United in early January, the team climbed out of the bottom four. However, this proved to be only a temporary abatement of the club's problems at that time. Despite bringing great performances from striker Dave Waller, who equalled the club's record for goals in consecutive games – eight – Chesterfield were relegated in the penultimate game. The following season saw Chesterfield reach the play-off final at Wembley after spending almost the entire season in the top seven, underlying Hart's ability and promise as a young manager. The team was defeated 0–1 by Cambridge United for whom Dion Dublin scored the winning goal. In February 1990, he gave 19-year-old Sean Dyche his Football League debut. Given no funds for squad improvement for the 1990–91 season, results and form were extremely indifferent. He was sacked on New Year's Day, 1991. Leeds United Hart then moved into youth coaching firstly at Nottingham Forest, and then subsequently took charge of Leeds United's fledgling academy. Hart's proteges won the FA Youth Cup in 1993 and 1997 and formed the backbone of the Leeds side that reached the Champions League semi-finals in 2000–01. With International players such as Harry Kewell, Jonathan Woodgate, Ian Harte, Alan Smith, Gary Kelly, Paul Robinson, Matt Jones and Stephen McPhail. Nottingham Forest Hart then returned to take charge of Nottingham Forest's academy after a high-profile fall-out with Leeds manager George Graham over the promise of Jonathan Woodgate. Forest's Under-19 side became immensely successful winning the Under-19 title in 1999–2000. As the first team were faltering, and the club spiralling further into debt, players such as David Prutton, Jermaine Jenas, Keith Foy, Chris Doig, David Freeman, Kevin Dawson, Gareth Williams, Richard Cooper and Gareth Edds were blooded, with a further line of players including Barry Roche, Andy Reid, Brian Cash, Eugen Bopp, John Thompson and Michael Dawson following subsequently. On 12 July 2001, Hart was promoted from Youth Academy Director to manager, succeeding David Platt, who had recently left the club to