A goal in either half saw the Spireites fall to a 2-0 defeat to Maidenhead United at York Road.
James Rowe made two changes to the starting XI as Will Evans and Martin Smith came in for Fraser Kerr and the suspended Curtis Weston.
Both sides had to contend with the strong Berkshire wind swirling around York Road and chances were at a premium.
Dan Sparkes had the first chance of the game; his 25-yard free-kick didn’t curl enough and went well wide of the post.
After 20 minutes, Maidenhead took the lead. Sparkes made a run down the right-hand side before delivering a low cross for Nathan Blissett to stab home from close-range.
Chesterfield almost found an immediate response when Alex Whittle burst through on goal. His shot was saved well by Taye Ashby-Hammond and just evaded Liam Mandeville.
The hosts looked to add to their lead just before the half-hour-mark. Remy Clerima’s dangerous cross went all the way across the box without a touch.
Chances again dried up and the Blues went into the break a goal behind – the first time that has happened under Rowe.
Jak McCourt had the first chance of the second half. He picked the ball up just outside the area, but his shot was straight at Ashby-Hammond.
Soon after, the home side doubled their lead. Josh Coley lifted the ball over to the back post where Sparkes fired home first time into back of the net.
The Spireites had a tougher mountain to climb after the second goal. Substitutes Nathan Tyson and Adi Yussuf linked up; the latter took aim, but his effort didn’t have the power on it.
Tyson looked to pull one back as he rose highest to meet a cross but his header looped over the crossbar.
Unfortunately, nothing seemed to fall for Chesterfield and the full-time whistle soon sounded to signal a second successive away defeat.
Chesterfield: G Smith, Carline, Evans (C), Gunning, Maguire, Whittle (Taylor 66), McCourt, M Smith (Tyson 57), Mandeville (Yussuf 57), Whelan, Asante.
Unused Substitutes: Kerr & Clarke.