The Spireites were condemned to a second successive defeat at the Technique Stadium as FC Halifax Town left with a 2-1 victory.
James Rowe made three changes with goalkeeper James Montgomery making his debut, replacing Grant Smith.
Gavin Gunning and Tom Whelan returned to the starting XI in the places of Josef Yarney and Jack Clarke.
Kairo Mitchelll worked well to open up space for the first chance of the evening; he steeped away from his defender and fired an effort low and towards goal, but Sam Johnson was equal to it.
The away side took an early lead with a 7th minute goal. Jeff King kicked up the ball from a free-kick and guided his shot past a crowd of players and past Montgomery who was unsighted.
Mitchell continued to look for his first goal for Chesterfield. He had two efforts – one of which was deflected into Johnson’s hands and one that was well blocked.
Just before the half hour mark, Halifax doubled their lead. An in-swinging cross from the right-hand side met the head of Jake Hyde who nodded home.
The game slowed down for the rest of the half with the Blues going into the break two goals behind.
Rowe made a change at half time with Nathan Tyson coming on for Alex Whittle. Joel Taylor also replaced Whelan ten minutes into the half.
The away side came close to increasing their lead early into the half. Billy Chadwick rolled the ball across goal, but Hyde missed the slide-in, which would have resulted in a goal.
Tyson almost reduced arrears on the hour mark. He latched onto a mistake in the penalty area and fired an acrobatic effort on goal which cleared the crossbar.
With 20 minutes to go, the deficit was halved. A mistake from the Halifax defence saw the ball roll to Mitchell; he controlled it and flicked his shot into the back of the net for his first foal since joining from King’s Lynn Town.
The Spireites continued to probe for an equaliser. In added time, Fraser Kerr took down the ball in the box and swing an effort that was pushed wide of the goal by Johnson. The full time whistle sounded moments later.
Chesterfield: Montgomery Carline, Kerr, Gunning (C), Maguire, Whittle (Tyson 46), Weston, Oyeleke, Whelan (Taylor 54), Mandeville (Clarke 79), Mitchell.
Unused Substitutes: Yarney, Dinanga.