The Spireites fell to a second successive defeat after Torquay United scored goals in either half and left the Technique Stadium with a 2-0 victory.
Manager James Rowe made five changes to the side that lost at Hartlepool United as Gavin Gunning, Alex Whittle, Martin Smith, Liam Mandeville and Kairo Mitchell returned to the starting line-up.
Josef Yarney, Joel Taylor, Curtis Weston, Jack Clarke and Nathan Tyson all made way; Jak McCourt and Adi Yussuf both returned to the bench.
The first chance of the game fell to Mitchell. The striker rose highest to meet Mandeville’s cross, but his header drifted wide of the goal.
However, the away side would take the lead in the 11th minute Jake Andrews’ pass-cum-shot was scuffed into the path of Connor Lemonheigh-Evans and he slotted the ball beyond Grant Smith.
Chesterfield wouldn’t let the goal bring them down and were the better team for the rest of the first half. Danny Rowe saw his header from Fraser Kerr’s cross saved by Lucas Covolan.
Just after the half-hour mark, the Blues came inches away from finding an equaliser. Martin Smith’s corner was headed towards goal by George Carline, but it was cleared off the line by a Torquay defender.
Rowe once again came close to opening his account for the Spireites. A curling effort from 25 yards flew the wrong side of the post and the away side would take the one-goal lead into the break.
Seven minutes into the second half, Chesterfield made their first substitution as Yussuf came on for Mitchell.
The striker almost made an immediate impact when he was put through on goal. He used his strength to create some space and flicked the ball over Covolan and towards goal, but it was cleared away inches from goal.
Laurence Maguire picked up the ball on the right-hand side after the clearance. The defender whipped in a cross that Yussuf headed to the back-post where Mandeville looked to nod home, but he couldn’t find the right connection.
Against the run of play, Torquay doubled their lead with just under 15 minutes to play. Billy Waters picked the ball up on the edge of the area and rifle his shot past Smith.
The Spireites continued to look for a way back into the game but it wasn’t to be, and the game ended 2-0.
Chesterfield: G Smith, Carline, Kerr, Gunning ©, Maguire, Whittle, M Smith (Whelan 81), Oyeleke, Mandeville (Clarke 75), Mitchell (Yussuf 52), Rowe.
Unused Substitutes: McCourt, Rowley.