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Boro's faint play-off hopes were extinguished with a disappointing display and a deserved 2-1 defeat to basement battlers Millwall.
Some poor defending twice allowed Millwall to score in the first half as Lions' striker Stefan Meierhofer was allowed free-headers at the far post.
Boro perked up after the break and pulled one back with an Emmanuel Ledesma free-kick but it was too little, too late.
Aitor Karanka opted to stick with the 352 shape from last week's 1-0 win away at Burnley with the only change at the back, Kenneth Ormeruo returning from a ban to slot in for suspended Daniel Ayala.
Millwall included former Boro man Nicky Bailey in midfield while ex-striker Scott McDonald was on the bench.
Boro played some neat, patient passing football in the opening spell as they tried to pick their way through the Millwall defence without finding a way through.
But Boro almost broke the deadline in the sixth minute as a poor touch by Bailey was seized on by Grant Leadbitter, who flicked inside to Danny Graham who nodded it back then burst towards the box and when Leadbitter slotted it into his feet the striker rifled in a low shot that sent keeper Forde full length to tip onto the far post and away.
But Millwall respond with a decent chance on 10 minutes as they won a corner on the left and when Martin curled it to the far post skipper Dunne arrived to put a free header just wide.
Then a minute later when another corner was scrambled away Martin scooped it back in towards lofty Maierhofer beyond the far post but he headed into the side netting.
And after another Martin ball into the Boro box was scrambled away Malone drilled in a 25 yard shot that was bravely headed clear by Chalobah.
And the visitors pressure told on 16 minutes as lively Martin curled in another cross from the left for STEFAN MAIERHOFER to power home a close range header.
A minute later a good Bailey ball sent Martin racing clear to send a 20 yard shot screaming over.
Boro went close on 19 minutes when a quick touch by Graham sent Jacob Butterfield into the box but his shot was blocked by keeper Forde then hooked away then Omeruo slammed the rebound low through a crowd and a foot wide of the far post.
Then on 23 minutes a lovely move saw Tomlin and Butterfield combine to carve down the right. Butterfield got to the byline inside the box then chipped back for Graham to direct a glancing downward header towards the near post but Forde dived to save.
Millwall threatened on 27 minutes as Malone over-lapped onto a Martin touch to cross to the far post where Maierhofer had arrived but alert Ledesma nipped in to thump it clear.
And Millwall got a second on 30 minutes with a carbon copy goal, Martin wriggling down the left to cross to the far post where unmarked STEFAN MEIERHOFER stooped to put a downward header inside the post.
Millwall could have had a third on 35 minutes as Malone crossed into the box for Woolford but as he turned to shoot Ledesma arrived to block and it deflected behind for a corner which was cleared.
Boro had a half-chance on 37 minutes as Tomlin brought down a Leadbitter flick on 30 yards out then turned and fired a hopeful low effort well wide of the far post.
And a minute later Tomlin skipped through two tackles to get within shooting distance but as he unleashed he was rattled by a Bailey challenge and the ball squirted weakly towards the keeper.
On 39 minutes Dean Whitehead was booked for a foul on Woolford.
Boro almost pulled one back on 42 minutes as Tomlin touche don to send Graham into the box then darted forward onto the return but had to stretch into his 12 yard shot and it screwed wide.
And just before the break Boro threatened again as Tomlin weaved from left to right across the edge of the box then pushed it wide for Butterfield to send a waist-high shot fizzing just wide.
HALF-TIME: BORO 0 MILLWALL 2
Boro attacked from the off as Ledesma tricked his way into the box from the left then squared for Tomlin to lay it back for Butterfield who touched inside for Leadbitter whose low shot got lost in a forest of legs before being hacked clear.
Then Tomlin won a free-kick wide on the left and Leadbitter's ball into the crowd almost dropped for Chalobah but a defender stretched to just poke it away.
Then on 53 minutes Ledesma curled in a cross from wide on the left that looked like it may dip in at the far post but it landed on the roof of the net.
And soon after Tomlin shrugged off his marker to find space on the edge of the box but his low shot was straight at the keeper.
On 58 minutes Tomlin was booked for a foul on keeper Forde.
On 61 minutes Millwall put on Morison for Williams.
Boro threatened on 64 minutes as Tomlin turned well onto a touch by Williams then flicked just beyond the far post from the edge of the box.
Boro won a free-kick 25 yards out to the left of the box on 69 minutes but Ledesma blasted it straight into the wall.
On 71 minutes they won a free-kick on the other side after Malone was booked for pulling back Adomah but Ledesma's curling ball was nodded behind for a corner.
On 72 minutes Millwall put on Abdou for Meierhofer and Boro put on Curtis Main for Leadbitter.
Millwall had a golden chance to seal it with a third on 72 minutes as Dunne knocked a long ball forward out of defence to send Morison storming forward with defenders in pursuit buthis low shot from 20 yards was easily saved by Konstantopoulos.
And they went closer still a minute later as Dunne sent Morison surging down the right and when he cut it back into the box Woolford stabbed it goalwards but Konstantopoulos went full length to push it away at the far post.
Boro won a free kick in the D on 79 minutes after Beevers bundled home Graham and the keeper ws booked for protesting.
And from the kick Boro clawed a goal back as EMMANUEL LEDESMA chipped over the wall and dipped it under the bar.
On 84 minutes Millwall put on McDonald for Malone and Boro put on Friend for Whitehead.
Millwall almost had a third in stoppage time as McDonald drilled in a low 20 yard shot that Konstantopoulos blocked and Martin – who had darted behind the defence - poked home the rebound but luckily the offside flag was up.
BORO (352): Konstantopoulos, Omeruo,Chalobah, Woodgate, Whitehead (Friend 84), Leadbitter (Main 72), Adomah, Butterfield (L Williams 58), Ledesma, Tomlin, Graham, Subs: Steele, Varga, Hines, Morris
MILLWALL (433): Forde; Edwards, Dunne, Beavers, Malone (McDonald 84); Bailey, Williams (Morison 61), Martin; Garvan, Woolford Maierhofer (Abdou 72).. Subs: Bywater, Robinson, Easter, Jackson
Ref: Darren Bond (Lancashire)
Att: 15,342 (335)
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