Two goals from Mohamed Eisa gave Cheltenham a 2-0 victory at the Proact in Jack Lester's first game in charge of the Spireites.
The newly-appointed boss made four changes to the starting XI with Tommy Lee, Ian Evatt, Jordan Flores and Kristian Dennis replacing Joe Anyon, Zak Jules, Andy Kellett and Gozie Ugwu.
Cheltenham had a good opening early on when captain Kyle Storer drove through the defence to face Lee one-on-one with the keeper making a good save.
Cheltenham keeper Scott Flinders failed to gather the ball following Louis Reed's shot and the loose ball fell to Evatt who fired wide.
A minute before half time, the deadlock was broken when Eisa received a pass from Jerrell Sellars before curling a low, right-foot shot past Lee.
Harry Pell latched onto a long ball in the area and Sam Hird made a last-ditch challenge to bring the forward down with the referee waving away the visiting team's penalty appeals.
Good build-up play from the Spireites ended with a shot from Diego De Girolamo which was blocked.
Reed went close to levelling when his free-kick proved challenging for Flinders who was forced to tipped the ball over the bar.
Eisa (69) added his and Cheltenham's second, controlling the ball well from Danny Wright's lay-off before finishing with ease.
Cheltenham almost scored a third when Sellars was denied by Lee.
Chesterfield: Lee, Hird, Wiseman, Evatt, Dennis (Ugwu 55), O’Grady, De Girolamo, Flores (Mitchell 55), Reed (McCourt 75), Weir(C), Briggs
Substitutes not used: Anyon, Rowley, Sinnott, Kellett
Cheltenham Town: Flinders, Grimes, Storer (C), Pell, Winchester, O’Shaughnessy (Cranston 44), Sellars, Eisa (Hinds 81), Graham (Wright 62), Morrell, Moore
Substitutes not used: Flatt, Atangana, Royle, Davey
Attendance: 5,305 (217 away fans)