Second-half goals from Liam Mandeville and Jack McKay saw the Spireites come from behind to win 2-1 at Hallam FC in their second pre-season fixture.
John Sheridan put out a senior side which included summer signings Anthony Gerrard and David Buchanan. A trialist lined-up in attack alongside Scott Boden.
Gerrard featured in a three-man rearguard alongside Laurence Maguire and Will Evans, with Buchan and Josef Yarney operating as wing-backs.
Keeper Archie Sneath had to make a save in the second minute to keep out Boden.
Buchanan swung over a free-kick from the right which was met by Maguire, who headed wide.
Hallam’s James Reed took a free-kick which went over.
Boden went close to bundling the ball home from close range after meeting the trialist’s low cross with Sneath just managing to scramble it away on the line.
The trialist himself then threatened inside the area with Sneath smothering his shot.
The hosts took a 13th minute lead from the penalty spot, Sam Smith sending Shwan Jalal the wrong way after Yarney fouled Will Wraith.
Boden put a looping header over from Buchanan’s cross while Robbie Weir’s long-range shot took a deflection off Boden and Sneath gathered the ball comfortably.
Smith went close to equaling midway through the half when his header from Curtis Weston’s cross hit the underside of the bar and into the grateful arms of Sneath.
The trialist also posed an aerial threat, heading over after getting on the end of a Buchanan corner.
Evans produced a good touch to set himself up for a surge into the area before a timely challenge cut his run short.
Sheridan made wholesale changes at the break with the side lining up as follows at the start of the second half: Trialist, Smith, Sharman, Hollis, Sheridan, Maguire, Weston, Rowley, Mandeville, Shaw, McKay.
Mandeville put over a low cross which just evaded Lee Shaw at the far post.
Mandeville then laid the ball off to Weston whose rising drive went over.
Charlie Wakefield was sent on as a 63rd minute replacement for Weston as Sheridan made another substitution.
Mandeville tried a shot which took a deflection wide and from the resulting corner, Haydn Hollis put his near post header just over.
The second penalty award of the match saw Chesterfield level through Mandeville after Joe Rowley was brought down inside the area.
A further change came in the 76th minute when teenage midfielder Jack Holmes came on in place of Maguire.
McKay struck the winner in the 81st minute after connecting well with Mandeville’s cross.
Shaw fired narrowly wide from inside the area after receiving the ball from Wakefield.
Spireites: Jalal, Buchanan, Evans, Yarney, Gerrard, Maguire, Weir, Smith, Weston, Trialist, Boden