The Spireites are through to the fifth round of the Buildbase FA Trophy after winning in a penalty shoot-out at Boston United.
They won 4-1 on penalties following a 1-1 draw in normal time, to set up a trip to Aldershot Town.
James Rowe made six changes from the defeat at Solihull Moors as academy product Dylan Wharton and new signings Martin Smith and Marcus Dinanga made their debuts.
George Carline returned to the starting line-up as did Joe Rowley and Liam Mandeville as Kyle Letheren, Joel Taylor, Jak McCourt, Tom Whelan, Akwasi Asante and Tom Denton made way.
The game started off at a frantic pace with both teams having good chances. Wharton was at full stretch to deny Andi Thanoj from a free-kick 25 yards from goal.
Rowley was unfortunate not to open the scoring for Chesterfield. One of four former Blues playing for Boston, Ross Fitzsimons, made two good saves to deny the midfielder his first goal of the season.
In the 17th minute, Rowley was presented with another great chance to open the scoring. The 21-year-old made his way towards goal before firing his effort into the side-netting.
Just before the half-hour mark, the hosts came closest to breaking the deadlock in the first half. Wharton failed to hold onto a free-kick, Jay Rollins hooked the ball towards goal, but Will Evans was on hand to clear off the line.
Josef Yarney had the last real opportunity of the first period when he made his way down the right-hand side and into the Boston area, but he snatched at his shot and the effort went over the crossbar.
Early in the second half, the home side took the lead. Joe Leesley’s corner flew all the way to the back post where Scott Garner powered his header home.
Boston almost doubled their lead soon after. Haydn Hollis gave the ball away to former Spireite Connor Dimaio, who blazed his shot well over the crossbar.
Chesterfield struggled to combat the wind working against them. A clearance from Fitzsimons bounced over Wharton and crashed off the crossbar.
However, with 15 minutes to go Rowe’s side found an equaliser. Substitute McCourt’s in-swinging corner was met by Hollis at the front post and the defender glanced his header past Fitzsimons.
As time ran out, both sides continued to cancel each other out and the game went to a penalty shoot-out.
Laurence Maguire scored the first penalty, squeezing his spot kick past Fitzsimons. The same couldn’t be said for Boston’s Jordan Burrow as Wharton made a fantastic save to deny the former Spireites striker.
The next three penalties were converted with Rowley and McCourt finishing with aplomb. Dimaio then put his effort wide to give Chesterfield the chance to win it.
Substitute Tom Whelan stepped up and hammered his penalty home to set up an away tie against Aldershot.
Chesterfield: Wharton, Yarney, Evans, Hollis, Maguire, Carline, M. Smith (McCourt 56), Weston, Rowley, Mandeville (Whelan 71), Dinanga (Asante 46).
Unused Substitutes: Clarke, Hutchinson.
