Chatterley was born in Birmingham and began his career as an apprentice at Aston Villa, turning professional in February 1962, with his league debut coming the following season.
In March 1971 he joined Doncaster Rovers on loan, where he first met Lawrie McMenemy, who was to have a considerable influence on his later career.
As the team struggled to shine in the Second Division, Chatterley became the butt of the crowd's frustration, and, in February 1975, he moved to Torquay United as player-coach, where he was to play a further 57 league games and score 10 goals.
In January 1990, Chatterley returned to The Dell as a youth development officer, and, in July 1991, once again became a coach under Ian Branfoot who had recently been appointed Southampton's manager.
In January 1994, following Branfoot's departure, he briefly acted as caretaker manager in tandem with Dave Merrington, taking charge of the team for one match, before Alan Ball's appointment.