The Spireites fell to a third defeat in a row after falling 3-1 at home to Woking.
Paul Cook made one change from the weekend as Jeff King replaced Ryheem Sheckleford, but the away side built-up a 3-0 lead by the 33rd minute.
A much-improved second-half performance followed as Liam Mandeville fired home a fifth goal of the season. However, Chesterfield’s efforts were not enough to mount a comeback
An early James Daly drive proved to be a warning shot as Woking took the lead after six minutes. Rhys Browne latched onto a long and squared it across the goal to Padraig Amond – the striker passed the ball home from close-range.
The visitors soon doubled their lead when a mistake by Ash Palmer allowed Daly through on goal, and he rounded Lucas Covolan before calmly finishing.
Chesterfield searched for a foothold back into the game and almost found on when Armando Dobra’s curling effort was tipped away by Craig Ross.
The Cards continued to press and claim the ball back from the Spireites; Josh Casey broke free from corner and forced Covolan into a smart save.
Woking soon made it three as former Spireite Jim Kellermann powered a header past Covolan from a Daly cross.
The shellshocked Blues came out for the second half with a point to prove. In the 49th minute, Dobra’s cut-back fell set-up nicely to Liam Mandeville and the midfielder fired a half-volley past Ross.
The game fell into a lull as the second half progressed with the hosts continuing to try and mount a comeback. Tim Akinola and Jez Uchegbulam came on to replace Darren Oldaker and Colclough.
Woking almost wrapped the game up with 20 minutes to go as Daly progressed into the penalty area before forcing Covolan into a strong save.
Uchegbulam provided some much-needed pace down the right-hand side and almost brought another goal as his cross was diverted over the crossbar by Rohan Ince.
The ball would not drop for the Blues would have to settle for a first league defeat at the Technique Stadium since October.
Chesterfield: Covolan, King (Sheckleford 82), Palmer, Grimes ©, Horton, Banks, Oldaker (Akinola 68), Mandeville, Dobra, Colclough (Uchegbulam 68), Quigley.
Unused Substitutes: Maguire, Jones.
Attendance: 5,499 (121 away)
