Jack Lester was denied a dream Chesterfield homecoming as visitors Cheltenham eased to a first away win in the league since February.
The club legend lost his first game in charge of the Spireites 2-0 and the many problems he will need to fix were laid bare.
A lack of creativity and cohesion in the final third, a lack of bite in midfield and lax defending resulted in a fifth straight defeat for Town.
The team who now haven’t won in nine matches started brightly enough, Jordan Flores having the game’s first effort, drilling a low shot well wide after being teed up by Louis Reed 20 yards out.
A lovely ball over the top from Scott Wiseman almost put Chris O’Grady in the clear, seconds before Kyle Storer did run clean through on goal at the other end, Tommy Lee making a vital save to keep the game goalless.
O’Grady was a busy man for the Spireites in the opening half an hour as the hists went direct, looking to work off the striker’s flick ons and knock downs - but they created little.
Lee was called into action a couple of times as the first half progressed, catching a couple of tricky crosses under pressure, Cheltenham having a similarly difficult time putting cohesive attacking play together.
An error from Cheltenham stopper Scott Flinders created havoc in his own box, the keeper letting a cross slip through his hands and sparking a scramble that ended in Ian Evatt’s off target shot.
Flinders got lucky again when a Flores shot bounced up off the tuf onto his shoulder before looping over the bar.
And as Town got on top, Kristian Dennis curled over the top from outside the area.
But the age old problem of failing to get a grip in the middle of the pitch aallowed Jerrell Sellars to dart through the centre and find Mohamed Eisa who took a touch, looked up and beat Lee from 20 yards.
The Cheltenham dangerman should have added his second the other side of the break, getting in behind Sam Hird and closing in on Lee, who watched as the shot mercifully slid the wrong side of the near post.
Hird was under pressure again when Harry Pell went through on goal, but this time the defender timed his challenge to perfection and Lee gathered, the referee unmoved by penalty appeals.
Lester made a double change 10 minutes after the break, replacing Dennis and Flores with Gozie Ugwu and Reece Mitchell, the latter straight into the action on a counter attack, cutting in and firing over.
Eisa remained a threat for the away side and should have done better when the ball dropped to him in the area after some dreadful Town defending.
He made no mistake on 69 minutes however, a ball up to Danny Wright nodded into a gaping hole in the heart of the home defence, Eisa stroking it past Lee from 18 yards.
A Louis Reed free-kick from 25 yards briefly caused the visitors alarm, before Flinders palmed it over his crossbar.
That was as close as Chesterfield came as the game petered out, Cheltenham largely comfortable for the remainder.
Chesterfield: Lee, Wiseman, Briggs, Hird, Evatt, Weir, Reed (McCourt 75), Flores (Mitchell 56), De Girolamo, Dennis (Ugwu 56), O’Grady. Subs: Anyon, Rowley, Sinnott, Kellett.
Cheltenham Town: Flinders, Winchester, O’Shaughnessy (Cranston 45), Grimes, Moore, Sellars, Morell, Storer, Pell, Eisa (Hinds 82), Graham (Wright 62). Subs: Flatt, Antangana, Royle, Davey.
Referee: Mr Ben Toner. Assistants: Mr Ian Dudley, Mr Lee Freeman.
Goalscorers: Eisa 44, 69
Yellows: Briggs 86, O’Grady 87
Attendance: 5,305 (217 away)