The Spireites took an early lead at home to Burton Albion in their final pre-season fixture before slipping to a 5-2 defeat.
Anthony Spyrou was put through on goal by Scott Boden in only the second minute and showed good composure to slot the ball past Kieran O’Hara for the opening goal.
Haydn Hollis made a great recovering challenge to block Liam Boyce’s shot.
Shwan Jalal made a good save to keep out Scott Fraser’s effort from the edge of the area.
Fraser scored a 12th minute equaliser after being put through on goal and rounding Jalal.
Chesterfield went close to regaining the lead when Spyrou’s shot came back off a post and the ball rebounded to Boden whose effort was saved.
Maguire did well to get back and make a timely block as Ryan Edwards threatened inside the area.
David Buchanan then fired wide following Boden’s lay-off and Maguire shot wide from distance.
Boyce (29) put the visitors ahead after meeting a corner with a header.
The same player extended Burton’s advantage a minute later with a finish from inside the area.
Ryan Edwards (34) added a fourth goal for Burton with a shot which looped into the net after Jalal’s touch saw the ball hit the bar and a post before going in.
Boden had a shot blocked moments before the half-time whistle was blown.
John Sheridan made a couple of changes for the start of the second half with Luke Coddington taking over in goal and Curtis Weston replacing Robbie Weir.
Five minutes into the second half, there was another change when Joe Rowley came on in place of Boden.
Just before the hour-mark, Rowley advanced towards the area from the halfway line and fired in a shot which went over.
Evans (60) pulled a goal back, heading in from a Liam Mandeville corner.
Spyrou was unlucky not to add a third a few minutes later with a low, angled shot which came back off the far post.
Spyrou went off a couple of minutes later with Jack McKay taking his place.
A double substitution in the 70th minute saw Jay Sheridan and Charlie Wakefield come on for Buchanan and Mandeville).
There was another change a minute later with Sam Wedgbury replacing Jonathan Smith.
Maguire shot over from the edge of the area as the Spireites looked to reduce the arrears.
Rowley then had an effort blocked, as did McKay after connecting with the rebound.
Weston had an effort deflected wide late on before Lucas Akins rounded off the scoring in stoppage time.
Spireites: Jalal (Coddington h/t), Buchanan (Sheridan 70), Yarney, Evans, Hollis, Maguire, Smith (Wedgbury 75), Weir (Weston h/t), Mandeville (Wakefield 70), Spyrou (McKay 65), Boden (Rowley 50)