Danny Whitaker bagged a brace but it wasn’t enough to prevent a 5th straight 1st round defeat for Spireites in the Carling Cup.
Ashley Grimes also scored twice and Dwayne Mattis put through his own goal to give Rochdale the win.
John Sheridan made four changes to the side that lost at Tranmere. Simon Ford, with a slight knock was missing, whilst Mark Randall, Jack Lester and Jordan Bowery moved to the bench.
In came Dean Holden, Derek Niven, Scott Boden and, for his first appearance since injury in February 2010, Aaron Downes. Drew Talbot moved from right back to right wing in a bid to up the feed to the front two.
Dale made just one change, ex Owls keeper David Lucas replaced Jake Kean who played in the loss at Hillsborough at the weekend to make his debut.
Speculation at Spotland was rife about Rochdale striker Chris O’Grady and a possible move to Sheffield Wednesday. It intensified when he was left out of the squad completely and just ahead of the kick off the move was confirmed.
Spireites, playing a familiar 4-4-2, opened well and delivered in more crosses in the opening few minutes than in the full game at Prenton Park. They took the lead when Boden laid the ball off for Whitaker, who stroked in an 18 yard low, inch perfect shot to beat Lucas.
Dale levelled when Jean-Louis Akpa Akpro’s strong left sided run led to him pulling back for Grimes to score.
Neat football and plenty of desire came from both sides ahead of the break and there were plenty of half chances for both sides throughout.
Dale began the second half the stronger and Akpa Akpro should’ve twice scored but fired wide.
Sub Jordan Bowery had the ball in the net on 90 only for an offside flag to intervene.
Jack Lester was upended for a penalty and Whitaker scored from the spot only for Mattis to slice in an own goal from a teasing Nicky Adams cross.
Grimes won it 9 minutes from the end when he squeezed in a Joe Widdowson cross from the near post to end the scoring in an excellent game which either side could have won.
Rochdale: Lucas 6; Darby 7, Trotman 7, Holness 6, Widdowson 6; Kennedy 6 (Thompson 97), Jones 7, Tutte 7, Adams 8; Akpa Akpro 7, Grimes 7. Subs (not used): Edwards, Twaddle, Marshall, Fagbola.
Goal: Grimes 19, 111, Mattis og 104
Chesterfield: Lee 6; Holden 7 (Lester 67/7), Mattis 6, Downes 7, Smith 7; Talbot 8, Allott 7, Niven 7 (Clay 113), Whitaker 7; Morgan 6, Boden 6 (Bowery 7/6). Subs (not used): Fleming, Randall, Gray, Darikwa.
Goal: Whitaker 10, 96 (pen)
Booked: Allott 116 foul
Ref: Scott Mathieson (Stockport)