Ten-man Coventry City's undefeated run came to an end at Glanford Park as Scunthorpe United came from behind to grab all three points.
Frank Nouble gave the Sky Blues a great start with his 17th minute opener but a straight red card for Reda Johnson midway through the first half gave the Iron an advantage they made the most of with Paddy Madden's 36th minute equaliser and Lyle Taylor's headed winner two minutes after the hour.
City boss Steven Pressley rang one change to the side that beat Yeovil Town 2-1 on Saturday, bringing in Simeon Jackson to make his first start for the club at the expense of the concussed Josh McQuoid.
The game very nearly got off to a shocking start when, after just 30 seconds, for Sky Blue Gary McSheffrey had a close range effort turned over the bar by Ryan Allsop.
The early chance set the tone for the early stages of the game which did yield more half chances for the home side.
City defended stoutly though and they were rewarded for their patience in the 17th minute when a lovely through ball from Jackson sliced the Scunthorpe back four in half and found Nouble who made no mistake and slotted into the bottom corner past Bobby Olejnik.
Travelling Sky Blues supporters' joy turned to anguish on 25 minutes though after City found themselves down to ten men when an off-the-ball altercation between Reda Johnson and Lyle Taylor saw referee Mark Haywood hand the Sky Blues skipper a straight red card.
The resulting free kick was delivered into the box and City never cleared the danger, which saw McSheffrey turn the loose ball into the net, although the Iron's prospective leveller was ruled out for offside.
The equaliser did come nine minutes before the break though as Scunthorpe tried to press the game with the one-man advantage.
McSheffrey got to the byline and cut a ball back for Madden who side footed a finish into the bottom corner past Allsop.
The earlier dismissal seemed tobe the driving force of an early change for City as Seb Hines came on to replace Jackson, boss Pressley opting to retain his wing-backs and leave Nouble to operate as a lone striker.
The system was one that the Sky Blues stuck with after the interval and it appeared to be serving them well.
The hosts did not register another shot on target until a minute after the hour when substitute Hakeem Adelakun dropped his shoulder to get around Ryan Haynes before firing low at the post with Allsop making a strong save.
Allsop could not do much a minute later though when the Iron took the lead. Madden got down the right and lofted in a cross for Taylor who powered a header past the City shot stopper to put the home side in front.
In the search for an equalising goal Pressley switched his formation with the introduction of Shaun Miller on 72 minutes in place of Andy Webster as the Sky Blues opted for a second striker and a flat back four.
The change gave City a greater attacking threat with Miller and Nouble up top although although the man disadvantage made chances few and far between.
One of those chances came in the last minute of normal time though when Jim O'Brien made a great run to latch on to a through ball from Jordan Clarke but lash his shot across the face of goal.
With five minutes of added time to see out the Sky Blues kept pressing and twice caused panic in the Scunthorpe area with two late corners, the second of which saw Allsop come from his goal to put another body in the box.
The Iron saw out the late threat though to grab all three points and end City's impressive unbeaten streak.
Attendance: 2,866 (379 Sky Blue Army)
Coventry City: Allsop. Willis, Webster (Miller 72), Johnson (c), Clarke, Haynes, O'Brien, C Thomas (Swanson 68), Fleck, Nouble, Jackson (Hines 41)
Subs: Burge (GK), Pugh, Phillips, Tudgay
Scunthorpe Utd: Olejnik, McAllister, Canavan, Sparrow, Madden, Hawkridge (Adelakun 55), Taylor (Kee 87), O'Neill, McSheffrey (c) (Myrie-Williams 81), Williams, Llera
Subs: Weaver (GK), Dawson, Boyce, Sutton