The Spireites slipped to a 2-1 defeat at Harrogate Town after a superb goal from substitute James Berry had seen them draw level.
An even hard-fought first half saw both sides threaten but the home side probably came the closest to breaking the deadlock after Muldoon saw a header hit the crossbar and Duke-McKenna forced an alert save from Ryan Boot. Will Grigg went close at the other end but the home defence stood firm.
All the goals came in the second half with, sadly, Berry’s leveller not enough to earn a share of the spoils.
The Spireites arrived at Wetherby Road for their first Football League encounter against Harrogate knowing their impressive away form will need to continue if they are to end the unwanted record of never having beaten the Sulphurites in four attempts to date.
Harrogate’s form has been patchy, they’ve suffered five home league defeats but they’ve also knocked high-flying Wrexham out of the FA Cup at their compact ground after Jack Muldoon scored the game’s only goal.
Paul Cook chose to make just one change from the side that started the previous league fixture: in came Liam Mandeviile as Berry had to settle for a place on the bench.
The game started in crisp and dry conditions as the sun disappeared over the horizon; the Spireites kicked off defending the end that housed their noisy supporters.
The game’s first threat came from Harrogate after four minutes when Toby Sims ran 40 yards into box but was dispossessed and the danger averted.
Great work at the other end by Grigg and Mandeville saw the Spireites gain their first corner kick; it came to nothing and Harrogate broke well with Stephen Duke-McKenna receiving the final ball and showed his pace well.
The home side broke quickly from defence and missed a great chance after Muldoon fed Duke-McKenna; his shot was tipped away for a corner that came to nothing.
It had been a very even game but slowly the Spireites were starting to build some momentum in several promising moves.
Ollie Banks did what he had to do as Muldoon burst down the left wing; he picked up the first yellow card for Chesterfield. Moments later he hit a goalbound shot from just inside the area but Josh Falkingham, making his 300th appearance cleared to safety.
Two minutes were added at the end of the half but it came to nothing as neither side were able to fashion a clear opening.
An early let off for the Spireites in the second half as Duke-McKenna burst through into; thankfully an offside decision was given.
Referee John Mulligan awarded a very contentious free-kick just outside the area in the 56th minute. Duke-Mckenna’s free clattered the woodwork and Toby Sims was on hand to hit home the loose ball.
Three minutes later Armando Dobra had his on-target hit blocked and moments later went close but just couldn’t find an opening.
It was proving hard to create anything of note so Cook made four changes with an immediate impact. Berry received wide left, cut inside and hit a super curlingshot into the top corner, des[pite the efforts of Zico Asare to keep the ball out.
All of a sudden there was a new spark to Chesterfield’s game
With three minutes to go it looked like the home side had nicked it. A superb diagonal ball from Duke-McKenna found substitute Josh March at the far post who slotted neatly only to see an offside flag.
Five minutes were added and Harrogate took the lead in the 91st minute after March had a shot saved and Dean Cornelius followed up to hit home.
Sadly there was no way back for the Spireites as Harrogate fought tenaciously till the final whistle to seal a dramatic win
Chesterfield: Boot, Naylor, Grimes, Oldaker (Berry 76), Grigg, Dobra, Berry, Gordon (Madden 76), Markanday (Araujo 76), Banks, Tanton (Colclough 76)
Unused substitutes: Rinaldo, Williams, Jacobs
Referee: John Mulligan
Attendance:3,686 including 1,058 chesterfield fans
