A late Scott Boden goal was not enough for a Spireites comeback as two quick fire second half goals gave Woking a 2-1 win at the Proact.
John Sheridan made one change to the side that drew 2-2 with Boreham Wood at the weekend as Robbie Weir replaced the suspended Laurence Maguire.
Liam Mandeville had the first shot of the game from just outside the box. However, the shot was easily claimed by Craig Ross in the Woking goal.
His strike partner, Scott Boden, was involved with a couple of chances in the opening exchanges. He floated a cross into the Woking box that just evaded a group of Chesterfield players.
Mandeville then tried his luck in the 22nd minute; his shot was deflected into the path of Boden, but he could only put the ball over the bar at full stretch.
The hosts continued to pressure the National League newcomers. Boden was this time denied by Ross as the two sides went into the break goalless.
Minutes into the second half, the Spireites came close to taking the lead again. A ball into the box fell to Boden and the striker saw his shot whistle over the crossbar.
In the 52nd minute, the away side took the lead. Flowing play allowed Tyreke Johnson space to whip in a cross, which Ibrahim Meite eventually bundled in.
Nine minutes later, Woking doubled their lead. Dave Tarpey stood over a free-kick from 25-yards out which he curled into the top left corner and out of Shwan Jalal's reach.
Sheridan’s side reduced the lead with just three minutes to go. After some brief pinball in the box, Boden headed home from close range to halve the deficit.
Unfortunately, a comeback was not on the cards as the referee brought the game to an end with Woking securing a 2-1 win.
Spireites: Jalal, Smith (Sheridan 65), Yarney, Evans, Hollis, Buchanan, Wedgbury (McKay 56), Weir (Weston 65), Rowley, Mandeville, Boden
Attendance: 3,927 (97 away)