Goals in either half from Laurence Maguire and Ched Evans secured the win for the Spireites.
Manager Keith Hill made six changes to the side that started against Carlisle United on Saturday. Harrison McGahey, Jim McNulty, Aaron Morley, Reuben Noble-Lazarus, Sanmi Odelusi and Nathaniel Mendez-Laing were all given the nod for the tie.
Dale had a couple of early opportunities, as they dominated during the opening period.
After chasing down a ball which looked destined to go behind for a goal-kick, Reuben Noble-Lazarus delivered into the area for Ian Henderson who hit narrowly wide of the target.
Moments later, Henderson was in on goal again, but he could only send his effort over the bar.
With 11 minutes on the clock, Mendez-Laing forced Lloyd Allinson into the first save of the game. Mendez-Laing’s effort at the near post stung the palms of the ‘keeper, as it was sent round the upright.
Odelusi capitalised on a loose ball midway inside the Chesterfield half, and after breaking through on goal, saw his effort go wide of the target.
Rochdale continued to dominate but they went behind in the 25th minute. Laurence Maguire headed home from a corner ball against the run of play to open the scoring.
Before the half was out, Dale had several good opportunities to level the scoring.
Matthew Lund saw a volley at the back-post tipped over the bar and Noble-Lazarus had an effort deflected into the hands of the ‘keeper from the resulting corner.
During stoppage time, Lund was denied on the line, as his header was hooked away by the visitors.
HT: ROCHDALE 0-1 CHESTERFIELD
There was a change in personnel for the start of the second half, as Steven Davies replaced Noble-Lazarus.
Three minutes into the second half, Dale were reduced to 10 men as McNulty was dismissed after receiving his second yellow card of the game.
Maguire had the first chance of the half, as he rose highest to meet a corner ball and headed wide of the target.
A double substitution soon followed, with Jamie Allen and Donal McDermott making their return from injury to replace Odelusi and Mendez-Laing.
In a bizarre passage of play, the Spireites doubled their advantage. Allinson appeared to pick up a back-pass inside his own area, and as the referee allowed play to continue, the visitors hit Rochdale on the break. A raised flag against the offside Ched Evans didn’t come and he finished low beyond Logan.
The visitors came close to a third a few minutes later, as a snapshot, which was sent goal wards from a throw in, was tipped wide of the post by Logan.
In the 66th minute, Chesterfield were also reduced to ten men, as Anderson received a straight red card for a foul on Davies, who proved to be a handful for the Spireites.
After the dismissal, the lions’ share of the play swung in favour of Dale, with Keith Hill’s side asking all of the questions before the game was out.
Allen’s overhead kick, which looked destined for the back of the net was hooked away on the line. Moments later and he came close again, this time he was denied by a wonderful save from Allinson at his near post.
Dale continued on the ascendancy but they couldn’t find a way past the goalkeeper. McDermott was kept out at the near post by the stopper, and that was before Lund’s half volley was palmed wide of the post.
FT: Rochdale 0, Chesterfield 2.