Already losing at half time, the ten-man Spireites were blown away in the second half, falling to a 5-0 loss in exiting the FA Cup at the hands of Wycombe Wanderers.
Chairboys striker Paul Hayes flicked home a header three minutes before Scott Kashket doubled from six yards as the Spireites soon faced a two-goal first half defecit.
The host's task grew all the more unlikely when Jon Nolan received a straight red for a late tackle midway through the second half. Kashket's second, followed by Anthony Stewart's goal after Ryan Fulton's dropped cross then a Kashket hat-trick strike to make it five ensured the Spirietes were well beaten.
The Chairboys scored three goals inside a crucial seven-minute spell in the second half with Scott Kashket completing his hat-trick.
On a day to forget for the Spireites, Jon Nolan was sent-off in the 64th minute.
There was an early effort from Wycombe when Joe Jacobson put a free kick narrowly wide.
Jay O’Shea, who scored with an impressive free kick against Bristol Rovers last week, was looking to repeat the feat, but his effort was well off-target.
Ian Evatt then put a header on target, but it lacked the power to test Jamal Blackman in the visiting goal.
Ryan Fulton made a fine save to keep out Luke O’Nien’s shot from 25 yards, diving to his left to turn the ball round the post.
Wycombe took the lead in the 21st minute when Kashket ’s cross from the right was met by a glancing header at the near post from veteran striker Hayes.
Fulton produced another good stop to save Adebayo Akinfenwa’s low 20-yard effort.
The visitors increased their lead when Dominic Gape chipped into a packed area, the defence failed to clear and the ball fell to Kashket (24) who drilled a low shot past Fulton.
Chesterfield were struggling to pose much of an attacking threat and manager Danny Wilson elected to make a change before the break with Ched Evans joining the action as a 33rd replacement for Reece Mitchell.
Nolan fired in a low drive distance which was blocked. The midfielder was also in the thick of the action soon after the re-start with a header which was comfortably gathered by Blackman.
After Jacobson put a free kick just wide, Evans shot straight at Blackman after Dion Donohue played the ball to him inside the area.
There was a second change for the Spireites on the hour-mark when Kristian Dennis came on in place of Jake Beesley.
The Spireites were reduced to ten men in the 64th minute when Nolan was shown a straight red card following a late challenge on Gape.
Kashket (70) made it 3-0 to Wycombe, slipping the ball past Fulton after being put through on goal.
Kashket and Hayes both had efforts saved before Anthony Stewart (75) added a fourth, sweeping the ball home after Fulton failed to keep hold of it from a corner.
Kashket completed his hat-trick two minutes later after dispossessing Gary Liddle, who appealed in vain for a foul, before advancing into the area and slotting past Fulton.
Evans fired over as the Spireites went in search of a consolation goal.
Chesterfield: Fulton (gk) - Liddle (c), Evatt, Anderson - Donohue, Mitchell (Evans 32'), O'Neil, Nolan, Ariyibi - O'Shea, Beesley (Dennis 60')
Subs not used: Allinson (gk), Gardner, Dimaio, Simons, Maguire
Wycombe Wanderers: Blackman (gk) - Harriman, Jacobson, Stewart, Pierre, Gape (Bean 69'), O'Nein, Bloomfield, Hayes (c), Akinfenwa, Kashket (Cowan-Hall 81')
Subs not used: Richardson, Jombati, Thompson, Wood, De Havilland
Wycombe Wanderers: Hayes 21', Kashket 24' 69' 76', Stewart 74'
Attendance: 3,685 (483 away fans)