Mick McCarthy's men went down 2-0 against Stevenage at Broadhall Way. Felipe Morais put the home side ahead from the spot in the 51st minute, before Jordan Burrow's low drive made it two with 15 minutes remaining.
Lukas Jutkiewicz put Boro ahead at the Riverside Stadium, but goals from Markus Carver and Piero Mingoia sealed a memorable win for the League Two outfit.
The match between Rotherham United and Sheffield Wednesday kicked off 15 minutes late due to congestion outside the New York Stadium, but the home side did not have to wait long for Ben Pringle to open the scoring.
A well-taken free kick from Rhys McCabe drew the Owls level, but Lee Frecklington put the hosts ahead once more after 38 minutes. Wednesday had to play the final 11 minutes with 10 men after Jermaine Johnson was sent off for an off-the-ball incident.
Stevenage 2-0 Ipswich, Middlesbrough 1-2 Accrington, Rotherham 2-1 Sheffield Wednesday