Early goals from Mo Besic and Stewart Downing saw Middlesbrough to a comfortable 2-0 victory over the Blues at Portman Road. Besic netted the opener on 12 and Downing added the second four minutes later following an error from Blues skipper Luke Chambers with Town never looking like taking anything from the match.
Janoi Donacien and Jordan Graham returned to the Blues 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 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.
After such a lacklustre half, Paul Hurst’s side needed to dramatically up their game in the second half to maintain their unbeaten home record let alone end their long winless run.
It was little surprise that Hurst made changes ahead of the second half with Edwards and Freddie Sears replacing Graham and Jackson.
And Town should have pulled a goal back two minutes after the restart. Donacien whipped in a cross from the right and Ayala just did enough to force Jon Nolan to head across the goal and wide rather than into the net.
Two minutes later, Ward won the ball on halfway and fed Sears to his left. The former Colchester man took it on into the area before hitting a shot which flew not too far over with the Portman Road crowd beginning to get behind their side.
Town continued to have most of the ball but without being able to find a way past the Boro backline. However, on 59 Chalobah sent over a dangerous low ball from the right which bounced across the six-yard box but too far in front of Ward.
But it was the Teesiders who came close to scoring the game’s third goal on the hour mark, Skuse heading Ayala’s goal-bound header off the line before one-time Town target Jordan Hugill’s rebound was blocked.
Boro kept up the momentum with Hugill claiming he had been fouled by Donacien as a cross came in from the right, however, the striker looked to have made a lot of little contact as he wasn’t going to reach the ball.
Moments later, George Friend cut in and struck a shot across the face of goal, then soon after Hugill also shot wide.
The on-loan West Ham man was replaced by Britt Assombalonga seconds later, then on 69 Martin Braithwaite was swapped for Paddy McNair.
Town forced Randolph into his first save of the evening in the 72nd minute, and what a save it was. Edwards found his way blocked on the edge of the area and the ball was stabbed out to Chalobah, who struck a powerful low strike through a crowd of players which Randolph somehow got across to and palmed past the post.
With 14 minutes remaining Andre Dozzell was given his first taste of competitive first-team action under manager Hurst, the Portman Road crowd cheering the local boy’s introduction for Nolan.
Dozzell’s tidy passing was evident from the off and soon after his introduction he played a clever reverse ball into the path of Sears, who won a corner which eventually came to nothing.
Five minutes from the scheduled end, Chambers made a superb double challenge on Downing and then sub Sam McQueen as the pair broke into the Town area after the Blues had been dispossessed midway inside their own half.
On 87 Edwards smashed a powerful shot which looked to be on its way into net following a corner but his strike hit Nsiala and deflected harmlessly wide.
Late on, McNair sent over a dangerous ball for Boro which Assombalonga failed to get a touch on, then moments before the end Skuse nodded over.
The whistle was greeted by muted applause from the Blues support, Town having been better in the second half and having kept going throughout, despite it looking unlikely that they would get anything out of the game.
The Blues huffed and puffed but but lacked confidence and quality, only rarely - Nolan’s early header, Sears’s strike over soon afterwards and Chalobah’s effort saved by Randolph - looking like they might pull a goal back against a well-organised Boro team, who came closer to adding to their lead when Skuse nodded Ayala’s header off the line.
The match was effectively won in the first 16 minutes with the two poor goals which were gifted to the visitors with individual mistakes again playing a large part in the Blues’ downfall. Against a side with the quality and nous of Boro Town were never going to have a chance having given them a two-goal start.
The Blues’ winless run from the start of the season is now up to 11 in the Championship - plus the defeat at Exeter in the Carabao Cup - in addition to the final day of last campaign draw with Boro.
Town’s first home defeat of the season sees them drop back to 23rd in the table ahead of Saturday’s tough trip to Swansea ahead of the international break with the pressure increasing on manager Hurst.
Town: Gerken, Donacien, Nsiala, Chambers (c), Knudsen, Skuse, Chalobah, Ward, Nolan (Dozzell 76), Graham (Edwards 46), Jackson (Sears 46). Unused: Bialkowski, Spence, Downes, Edun.
Middlesbrough: Randolph, Shotton, Ayala, Flint, Friend (c), Besic (McQueen 82), Howson, Saville, Downing, Braithwaite (McNair 69), Hugill (Assombalonga 65). Unused: Lonergan, Batth, Fry, Gestede. Ref: Andy Madley (West Yorkshire). Att: 13,612 (Boro: 438).