The Spireites fell to a third successive defeat in the National League after a 3-2 loss away to Wealdstone at Grosvenor Vale.
John Pemberton made three changes from the weekend. Haydn Hollis, Tyler Denton and Nathan Tyson came in for Laurence Maguire, David Buchanan and Luke Rawson.
Chesterfield were awarded a penalty within the first minute after Tyson was taken out by Wealdstone goalkeeper Harry Isted. Tom Denton assumed responsibility and fired the spot kick low and hard into the bottom left-hand corner.
Unfortunately, Tyson had to go off due to an injury he picked up in the collision. He was replaced by Luke Rawson in the seventh minute.
The hosts found themselves on level terms by the 13th minute. Moses Emmanuel was allowed to head home Dennon Lewis’ cross from six yards.
Two minutes later, Wealdstone took the lead. A low cross from Lewis on the tight was turned in by Emmanuel for his second goal of the game.
The Spireites came very close to finding an equaliser through Rawson; the young forward found himself free in the area but couldn’t direct Jordan Cropper’s cross into the back of the net.
Pemberton made the decision to replace Jamie Sharman with Josef Yarney in the 36th minute. Both sides continued to find an all-important goal but the score stayed at 2-1 going into half time.
The first effort of the second half fell to Weston. The midfielder brought the ball down and turned, but his shot deflected into the arms of Isted.
Chesterfield had the ball in the back of the net in 65th minute. A ball over the top found Tyler Denton who crossed the ball for Weston to tap home. However, the referee ruled the goal out because of a handball.
With ten minutes to go in the game, Wealdstone scored to make it 3-1. Jacob Mendy was allowed to take aim and fire from range and his thunderbolt flew past Letheren and into the top left corner.
Two minutes later, Tom Denton reduced the advantage. He rose highest in the area to head home from Cropper’s long-throw.
The Spireites had another goal ruled out in injury time. Substitute Scott Boden was adjudged to have fouled the home side’s goalkeeper before Tom Denton tapped home.
Soon after, the referee brought the game to an end in Ruislip. Chesterfield face Stockport County in the FA Cup on Saturday.
Chesterfield: Letheren, Cropper, Sharman (Yarney 36), Evans, Hollis, Tyler Denton, Weston, Smith, Mandeville (Boden 84), Tyson (Rawson 7), Tom Denton.
Unused substitutes: Wharton & Butterfield.