Early goals from Mo Besic and Stewart Downing have given Middlesbrough a 2-0 half-time lead over the Blues at Portman Road.
Janoi Donacien and Jordan Graham returned to the Town line-up for Matthew Pennington, who was suspended for one game following Saturday’s red card, and Gwion Edwards, who dropped to the bench.
Donacien came into the team at right-back with Graham on the left of midfield, while Grant Ward moved to the right. There was no place in the Middlesbrough 18 for ex-Blues skipper Grant Leadbitter.
Town saw plenty of the ball early on and passed it around but without getting into dangerous areas.
However, the visitors took their lead via their first serious attack in the 12th minute. Besic brought the ball forward from halfway unchallenged and hit a 25-yard strike which cannoned off Toto Nsiala, knocking the defender over.
The loose ball fell kindly for the Bosnian, giving him a free run at goal and he struck a low shot from the edge of the box past Dean Gerken to his right.
Four minutes later it was 2-0. Skipper Luke Chambers played a loose pass from the edge of the box straight to Downing on the Middlesbrough right and the ex-England international cut into the area and hit a low shot which hit the net off Donacien, leading to brief boos from the Blues support.
Town set about trying to get back into a game which already looked lost but without creating anything until the 25th minute when a Ward cross caused brief hesitation in the Teessiders’ defence before the danger was averted.
Daniel Ayala was fortunate referee Andy Madley failed to spot his late, studs-up challenge on Cole Skuse in the 28th minute otherwise the former Canary might well have seen at least a yellow card.
Town failed to make much impression on a Boro side happy to sit back on their two-goal lead until the 42nd minute when Donacien crossed from the right and Jonas Knudsen looped a header over the bar at the far post.
Three minutes later, Trevoh Chalobah sent a low ball into the box from midway inside the Boro half on the right but no Blues player was able to get a touch before Boro keeper Darren Randolph claimed.
Ayala looped a header over the bar just before the whistle which was met by further boos from an understandably frustrated Portman Road crowd.
The Blues had gifted Boro their two-goal and subsequently looked to have little idea of how to break down a visiting team largely happy to sit back and hold on to their lead, presumably well aware of Town’s lack of attacking threat this season.
Paul Hurst’s side will have to dramatically up their game in the second half - with changes at the break looking certain - if their long winless run is to come to an unlikely end in the second half.
Town: Gerken, Donacien, Nsiala, Chambers (c), Knudsen, Skuse, Chalobah, Ward, Nolan, Graham, Jackson. Subs: Bialkowski, Edwards, Spence, Sears, Downes, Dozzell, Edun.
Middlesbrough: Randolph, Shotton, Ayala, Flint, Friend (c), Besic, Howson, Saville, Downing, Braithwaite, Hugill. Subs: Lonergan, Batth, Assombalonga, McQueen, McNair, Fry, Gestede. Ref: Andy Madley (West Yorkshire).