Chesterfield’s decade-long EFL Cup drought was stretched as after taking the lead they bowed out 3-1 in the first round after three Rochdale second half goals.
Rochdale almost took an early lead themselves when debutant Samni Odelusi headed a cross back into the six-yard box, but Donohue reacted fastest to clear.
Chesterfield countered and Ched Evans struck powerfully from the edge of area, his shot stinging the hand of Lillis and going out for a corner.
Joe Rafferty sent in an inviting cross from the right for Rochdale, but Calvin Andrew was unable to send it goalwards and it bounced wide of the post.
The home side were dominating and Andy Cannon exchanged a series of passes with both Donal McDermott and Rafferty before delivering a low hit ball in towards Andrew whose strike sailed over the bar.
Countering once more Gboly Ariyibi received the ball from Dimaio and swung it into the box from the right wing, Evans was oncoming but Dale’s ‘keeper got there first to catch.
The deadlock was broken with a moment of brilliance from Paul McGinn (31), the full-back received the ball from O’Shea, looked up and launched a stunning shot from 27-yards straight into the far corner.
Henderson was the first to react for Rochdale, but the striker’s similarly audacious effort came off of the side of his boot and went both high and wide.
Gary Liddle’s cross deflected off of a ‘Dale defender and into the path of O’Shea who flicked it back towards Evans, but the Welshman’s cross was blocked and cleared.
With just minutes of the half remaining the home side won a freekick on the edge of the area, former Spireites’ loanee McDermott took the kick and sent it over the wall but narrowly past the post.
The home side equalised from their first attack of the second half, Henderson (47) jumping highest to meet an inviting free-kick from Allen.
Evatt was left unmarked on a corner and as Connor Dimaio’s ball fell in front of the centre-back he looked set to score but his shot was scuffed and sent wide.
Rochdale took the lead when McDermott charged down the wing and cut inside, the former Spireites winger drove a ball across the goalmouth that deflected off a Spireites defender and into the path of Cannon who’s shot struck Donohue (53) and dribbled into the right hand corner.
Receiving the ball on the right hand-side, McGinn combined for a one-two with Ariyibi and then delivered in a cross that floated just over the bar.
Rochdale almost extended their lead when Henderson found himself free just inside the area, McGinn’s challenge failed to stop the striker who blasted it goalwards, but substitute Charlie Raglan was on the line to clear.
Raglan’s clearance went straight back to Rochdale who attacked once more, Henderson picked up the ball on the edge of the area and hit it at Fulton who parried in front of him.
Manager Danny Wilson gave a debut to teenage winger Curtis Morrison from the bench as he went in search of an equaliser, and Morrison was nearly through after charging down the left-hand side, but his touch took it away from him as Dale cleared.
Running onto a long ball from Fulton, Evans looked up, took a touch and attempted to flick it above the ‘keeper who stretched to tip it over the cross-bar.
Ariyibi tried the same minutes later after being sent through by Dimaio, but unlike Evans his shot failed to trouble Lillis who easily caught.
Rochdale stretched their lead in the 76th minute when Andrew’s low driven cross went past Fulton and was slid home from close-range by substitute Mendez-Liang.
With time almost up, Dimaio floated in one final cross towards Morrison but his header was caught by Lillis as the referee blew his whistle for full-time.