Cedric Kipre’s own goal just before the break has given Middlesbrough a 1-0 half-time lead over the Blues at the Riverside, George Hirst having seen a penalty saved shortly beforehand.
Town boss Kieran McKenna named the same side which beat Norwich City 3-1 12 days ago with Sammie Szmodics and Sindre Walle Egeli considered fit enough to start despite being withdrawn from their international squads early last week.
Middlesbrough made four changes from the team which fell to a 1-0 loss at Portsmouth, their first Championship defeat of the season prior to the break, with Luke Ayling, Aidan Morris, who returned late from international duty with the US, Kaly Sene and Sontje Hansen all dropping to the bench and Alan Browne, Delano Burgzorg, one-time Town target Morgan Whittaker and David Strelec coming into the team.
The Teessiders, who had Hayden Hackney, who turned down a £15 million move to the Blues in the summer, in their midfield, switched to a back four from a three-man backline.
The game got off to a tentative start with the home side seeing most of the ball but not threatening, while Town won a couple of early free-kicks in the opposition half which came to nothing.
Hackney struck the first effort of the match in the 12th minute but the former England U21s effort flew over.
Within a minute, Leif Davis gifted the ball to Tommy Conway on the right of the box but the former Bristol City forward’s cross was diverted out for a corner by Kipre. The corner was taken twice following some wrestling between Conway and Jaden Philogene before the initial kick had been taken.
The Blues’ first chance came in the 17th minute, Szmodics, Philogene and Jens Cajuste combining before the Swedish international played in the overlapping Davis, who cut across to Szmodics, whose first-time effort was blocked by home skipper Dael Fry.
The ball eventually ended up back with Cajuste but his cross from the corner of the penalty area was too high for George Hirst at the far post.
Town briefly took charge, although while still scruffy at times, and on 20 Alfie Jones was booked for fouling Cajuste on halfway as the Blues broke.
Three minutes later, Hirst played a ball in behind the Boro backline for Philogene on the left, the former Aston Villa man cut in but his low shot was blocked.
The Teessiders subsequently had a spell on top and weren’t too far away from going in front in the 26th minute when Hackney skipped into the area, Cajuste pulling out of a tackle for fear of a trip, before hitting a strike which clipped Azor Matusiwa on its way wide.
Town put together their best move of the match in the 31st minute, one which should have resulted in a penalty.
Skipper Dara O’Shea played a superb cross-field pass to Davis wide on the left, the full-back sending over a brilliant first-time ball to Hirst, whose goalbound effort was stopped by Fry, clearly with an outstretched arm. The Blues’ players protested vehemently but referee Matt Donohue remained unmoved.
From the resulting corner, the ball was cleared to Walle Egeli on the edge of the box but the Norwegian blazed deep into the stand behind the goal.
Town may well have still been bristling about the penalty moments later when keeper Alex Palmer was forced to make two brilliant saves to keep the scores level.
Cajuste and Matusiwa both missed tackles allowing Strelec to burst way on the right of the area from where he cut across to the unmarked Conway, whose strike was closed down superbly by Palmer. The loose ball fell to Hackney, who worked himself room for another shot, which caught O’Shea on its way through and Palmer again brilliantly saved, this time tipping over.
From the corner, the Blues, the ball was cleared to Browne on the edge of the box was blocked, Town failing to get it away before Browne was able to hit another effort which was again stopped with Town again struggling to get it out of the danger zone.
As the game opened up, Fry did well to get ahead of Szmodics virtually on the goal-line from a Davis cross from the left to head over.
The end-to-end action continued, Boro breaking on Town with Burgzorg somehow in acres of space on the left taking the ball on ball on before hitting a low shot across Palmer that the keeper pushed away to his left. The loose ball fell to Strelec, who somehow shot across the face and wide when it seemed easier to score. Palmer made his frustrations with the slowly retreating Walle Egeli very evident.
Four minutes later, the Blues were awarded a penalty. The ball was deflected wide to Davis on the left of the area and Callum Brittain pulled the full-back to the ground. This time referee Donohue, with his mind perhaps made up by having made the wrong decision earlier, pointed straight to the spot.
After a long delay, in which Brittain was booked, Hirst took the kick and hit it low to home keeper Sol Brynn’s right, the Boro number one palming it away, much to the delight of the home support.
It was Hirst’s second successive penalty miss, including his effort in the shootout at Bromley in the Carabao Cup, having scored his first at Birmingham on the opening weekend.
Two minutes into injury time, the Teessiders took the lead in fortuitous circumstances. Burgzorg crossed low from the right and Kipre kicked the ball against his own leg and past Palmer from the edge of the six-yard box to send the home fans into raptures.
That was the last action of a half which had started slowly before ending with opportunities galore, both sides spurning chances before Kipre’s own goal handed the initiative to Boro.
Town had had spells on top, but the home side probably more and really should have taken the lead in the period in which Palmer made three terrific saves and Strelec managed a miss that will almost certainly go viral in the days to come.
The Blues then spurned their chance from the penalty spot - having had an even stronger shout earlier when Fry handled - before the late own goal.
Town will need to tighten up at the back and make more of their opportunities in and around the area if they’re to get anything out of the game in the second half.
Middlesbrough: Brynn, Brittain, Targett, Jones, Fry (c), Hackney, Conway, Burgzorg, Whittaker, Strelec, Browne. Subs: McLaughlin, McGree, Ayling, Morris, Nypan, Sene, Silvera, Bangura, Hansen.
Town: Palmer, Furlong, O’Shea (c), Kipre, Davis, Matusiwa, Cajuste, Walle Egeli, Szmodics, Philogene, Hirst. Subs: Walton, Greaves, Young, Taylor, Nunez, McAteer, J.Clarke, Akpom, Azon. Referee: Matt Donohue (Manchester).