Spireites beat Tranmere for the first time in a knock-out competition when Craig Westcarr bagged a stoppage time goal at the end of an entertaining and topsy-turvy contest.
Adam McGurk opened the scoring before Alex Mendy levelled. Jordan Bowery put Chesterfield ahead before Enoch Showunmi and Mustafa Tiryaki gave Rovers the edge.
Late headers from Bowery and Westcarr sent Chesterfield, ever present in the history of the competition, into the Northern semi-final to equal their best ever run.
This was the 100th competitive meeting between these two old rivals and it got off to a lively start. Westcarr just failed to get on to the end of a Tope Obadeyi cross ahead of McGurk unleashing a first time unstoppable volley from 25 yards.
The outlook worsened for Spireites after Drew Talbot was stretchered off with mild concussion. Ole Soderberg saved from Lucas Akins as the home side struggled to find any form, though Rovers, winners of this competition in 1990, weren’t much more effective.
Then, just ahead of the break, from nowhere, Mendy unleashed a corker from close on 30 yards to level things up.
Obadeyi hit just wide early in the second half and Mendy’s cross eluded his colleagues as the home side stepped things up.
And they were soon ahead when Bowery headed from close range following Westcarr’s excellent delivery from the left.
Sub Showunmi levelled with a header from John Welsh’s free-kick and Rovers soon took the lead when Tiryaki picked up a loose ball and delivered a hopeful looping shot that Soderberg seemed to have under control, but he ended up helping it into the goal.
Bowery headed in from a Mendy cross to even things up again and, in the first minute of stoppage time, Westcarr headed in Danny Whitaker’s free-kick to win it for Spireites.
Off the field, Spireites have been charged by the FA for failing to control their players following a last minute fracas in the final minute against Yeovil, who have also been charged, following a Mark Allott foul and booking.
Additionally, Scott Boden has extended his loan at Macclesfield Town and he’s been joined there by Dan Gray, who had a spell at Moss Rose last season.
Chesterfield (4-4-2): Soderberg 5, Talbot 6 (Ford 19, 6), Downes 8, Mattis 6 (Whitaker 76), Smith 5, Mendy 7, Johnson 6 (Allott 76), Grounds 5, Obadeyi 6, Westcarr 7, Bowery 7. Subs (not used): Fleming, Clay.
Tranmere (4-5-1): fon Williams 6, Holmes 6, McChrystal 6, Taylor 8, Buchanan 6, Akins 7, Welsh 6, Weir 7, Bakayogo 6 (Showunmi 57, 7), McGurk 7 (Labadie 71), Tiryaki 6 (Power 85). Subs (not used): Coughlin, Raven.
Goals: Mendy 44, Bowery 54, 80, Westcarr 90+1 (Chesterfield), McGurk 9, Showunmi 69, Tiryaki 72 (Tranmere)
Bookings: Mattis (Chesterfield)
Referee: Geoff Eltringham (Tyne & Wear)