Middlesbrough's poor form in 2013 continued as they lost to Millwall.
Tony Mowbray's side, with just one win so far this year, fell behind when George Friend headed James Henry's cross into his own net.
Martyn Woolford made it 2-0 just before the break, firing in after Jason Steele denied Benik Afobe.
Curtis Main finished from two yards and Middlesbrough thought they had scored a late equaliser, but Scott McDonald's effort was offside.
Millwall, like Middlesbrough, have struggled for form this year and went into the game on the back of five successive league defeats.
Boro's unwanted record
Middlesbrough hold the worst record in the Championship in 2013 with four points out of 27, dropping from third to seventh in the table
They were the better side though and were the first to threaten in the 15th minute when Grant Leadbitter's free kick flew just wide.
Millwall took the lead with their second chance on goal 10 minutes later. Henry sent an inviting cross into the area where the unfortunate Friend, under pressure from Afobe and John Marquis, sent a header beyond his own keeper.
The home side almost immediately restored parity but Main's powerful header from Leadbitter's corner was blocked on the line by Nadjim Abdou.
Instead, Millwall added to their advantage five minutes before the break. The lively Afobe's shot was pushed away by Steele and the stranded keeper could only watch on as Woolford sidefooted the loose ball into the net.
With nothing to lose, Middlesbrough pressed forward in search of a goal and it duly arrived 15 minutes before time as Main tapped in after being picked out by Friend.
That set up a tense finish and Millwall were left hanging on at the end. Middlesbrough players were briefly celebrating in stoppage time when they though McDonald had turned in a late equaliser, but it was ruled out.
Middlesbrough boss Tony Mowbray:
"They were poor, poor goals for us to concede from a defensive point of view. We made it very difficult for ourselves.
"We didn't get the luck but we can't keep saying that. It is down to us to win football matches.
"Of course we are very disappointed and of course it has an effect on confidence. And of course it is very frustrating for the supporters here who have seen these results over the past few weeks. But do we still believe we can make the play-offs? Of course we do."
Millwall boss Kenny Jackett:
"It was a fantastic result and a great performance. Middlesbrough is a very difficult place to come and get a result so we have got to be delighted with it.
"We made a few changes and we went with two up top and it paid off for us. The boys worked very hard for it. It was a honest performance.
"Having looked at it I thought the one at the end was definitely offside. The officials got it right."
Live Text Commentary
Full Time The final whistle goes and the game is over.90:00 +4:25
The offside flag is raised against Scott McDonald. David Forde takes the indirect free kick.90:00 +3:13
Free kick taken by David Forde.90:00 +3:13 Booking
Booking David Forde shown a yellow card.90:00 +2:53
Foul by George Friend on James Henry, free kick awarded.90:00 +1:49
Free kick awarded for a foul by Benik Afobe on Stephen McManus. Jason Steele takes the direct free kick.89:39
Free kick awarded for an unfair challenge on Josh McEachran by Benik Afobe. Jason Steele takes the direct free kick.89:02
Josh Wright decides to take the corner short.88:14
Curtis Main challenges Alan Dunne unfairly and gives away a free kick. David Forde takes the direct free kick.86:51
Curtis Main takes a shot. Comfortable save by David Forde.86:43
Benik Afobe is penalised for handball and concedes a free kick. Free kick taken by Grant Leadbitter.85:44
Shot by Curtis Main from deep inside the penalty area misses to the right of the goal.81:18
Ishmael Miller takes a shot. Save by David Forde. Outswinging corner taken right-footed by Grant Leadbitter from the right by-line, save by David Forde.79:38
Outswinging corner taken from the right by-line by James Henry, clearance made by Andre Bikey.78:35
Nicky Bailey gives away a free kick for an unfair challenge on Benik Afobe. David Forde takes the direct free kick.75:29
Scott McDonald takes a shot. Save made by David Forde.74:22
Assist on the goal came from George Friend.74:22 Goal scored
Goal! - Curtis Main - Middlesbro 1 - 2 Millwall Curtis Main grabs a goal from deep inside the penalty box low into the middle of the goal. Middlesbrough 1-2 Millwall.73:30
Nicky Bailey gives away a free kick for an unfair challenge on Martyn Woolford. Free kick taken by Mark Beevers.71:50
John Marquis challenges Nicky Bailey unfairly and gives away a free kick. Andre Bikey restarts play with the free kick.
Andre Bikey challenges Benik Afobe unfairly and gives away a free kick. David Forde takes the direct free kick.69:23
The ball is crossed by George Friend, save made by David Forde.68:00 Substitution
Substitution Scott McDonald is brought on as a substitute for Marvin Emnes.68:00
Benik Afobe has an effort from just inside the box that misses to the left of the target.64:16
Corner taken right-footed by Grant Leadbitter, David Forde makes a comfortable save.63:52
Mustapha Carayol produces a cross, clearance made by Karleigh Osborne.62:57
Long distance shot from John Marquis misses to the left of the goal.62:07
Corner from the right by-line taken by Grant Leadbitter, Alan Dunne manages to make a clearance.61:24
Curtis Main takes a shot. Danny Shittu gets a block in. Outswinging corner taken from the right by-line by Grant Leadbitter.59:24
Mustapha Carayol takes a shot. Save by David Forde. Corner taken right-footed by Grant Leadbitter, clearance by John Marquis.57:50
Handball decision goes against Marvin Emnes. Free kick taken by David Forde.56:51
Shot on goal by Ishmael Miller from just inside the area clears the crossbar.56:22
Free kick awarded for an unfair challenge on George Friend by John Marquis. George Friend restarts play with the free kick.54:32
Corner taken by Grant Leadbitter from the left by-line, save by David Forde.53:45
Unfair challenge on Alan Dunne by George Friend results in a free kick. Direct free kick taken by Josh Wright.53:14
Grant Leadbitter takes a shot.52:39
The referee blows for offside against James Henry. Indirect free kick taken by Stephen McManus.50:24
Handball decision goes against Josh Wright. George Friend takes the indirect free kick.49:02
The ball is sent over by Mustapha Carayol, Mark Beevers gets a block in. Outswinging corner taken from the right by-line by Grant Leadbitter, Header from deep inside the area by Andre Bikey goes harmlessly over the crossbar.47:06
George Friend takes a shot. Danny Shittu gets a block in. Corner from left by-line taken by Grant Leadbitter.46:44
The ball is swung over by Curtis Main.45:01
The match restarts for the second half.45:01 Substitution
Substitution Mustapha Carayol on for Rhys Williams.45:01 Substitution
Substitution Ishmael Miller is brought on as a substitute for Kieron Dyer.45:00 +3:07 Half time
Half Time The players leave the pitch at half time.45:00 +2:26
Free kick awarded for a foul by John Marquis on Jason Steele. Jason Steele takes the direct free kick.45:00 +0:51
The ball is swung over by John Marquis, free kick awarded for a foul by Martyn Woolford on Andre Bikey. Jason Steele restarts play with the free kick.44:35
Foul by Alan Dunne on Curtis Main, free kick awarded. The free kick is swung in right-footed by Grant Leadbitter, save by David Forde.43:42
Centre by James Henry, Rhys Williams makes a clearance.43:05
Outswinging corner taken by James Henry.42:03
George Friend has a shot on goal from outside the area which misses left.41:32
The assistant referee signals for offside against Benik Afobe. Josh McEachran restarts play with the free kick.41:12
George Friend sends in a cross, clearance made by Karleigh Osborne.39:02
Assist on the goal came from Benik Afobe.39:02 Goal scored
Goal! - Martyn Woolford - Middlesbro 0 - 2 Millwall Martyn Woolford finds the back of the net with a goal from the edge of the penalty box to the bottom left corner of the goal. Middlesbrough 0-2 Millwall.38:55
Benik Afobe takes a shot. Save by Jason Steele.36:32
The referee blows for offside against Kieron Dyer. David Forde restarts play with the free kick.34:13
Outswinging corner taken from the right by-line by Grant Leadbitter.33:27
Corner from left by-line taken by Grant Leadbitter.33:15
Grant Leadbitter takes a shot. Save by David Forde.31:43
The referee blows for offside against Benik Afobe. Free kick taken by Stephen McManus.30:53
John Marquis is ruled offside. Jason Steele restarts play with the free kick.30:11
Corner taken by James Henry.29:23
James Henry takes a shot.28:55
Centre by Grant Leadbitter, Alan Dunne makes a clearance.27:34
Corner taken right-footed by Grant Leadbitter from the right by-line, clearance by Karleigh Osborne.26:43
Direct free kick taken by Stephen McManus.26:43 Booking
Booking The referee cautions Josh Wright for unsporting behaviour.26:32
Foul by Josh Wright on Rhys Williams, free kick awarded.26:00
The ball is swung over by Andre Bikey, comfortable save by David Forde.24:26
John Marquis provided the assist for the goal.24:26 Goal scored
Goal! - George Friend - Middlesbro 0 - 1 Millwall Headed own goal by George Friend. Middlesbrough 0-1 Millwall.23:56
Unfair challenge on Mark Beevers by Nicky Bailey results in a free kick. Free kick taken by James Henry.21:49
James Henry is penalised for handball and concedes a free kick. Indirect free kick taken by Andre Bikey.18:59
Martyn Woolford concedes a free kick for a foul on Curtis Main. Free kick crossed by Grant Leadbitter, clearance by Karleigh Osborne.18:16
The official flags Mark Beevers offside. Jason Steele takes the free kick.17:40
Free kick awarded for an unfair challenge on Josh Wright by Grant Leadbitter. Josh Wright takes the free kick.16:53
Martyn Woolford concedes a free kick for a foul on Marvin Emnes. Direct free kick taken by Andre Bikey.14:31
Strike on goal comes in from Grant Leadbitter from the free kick.14:31 Booking
Booking Karleigh Osborne goes into the referee's book for unsporting behaviour.14:05
Curtis Main fouled by Karleigh Osborne, the ref awards a free kick.13:28
Foul by Curtis Main on Mark Beevers, free kick awarded. Mark Beevers takes the direct free kick.10:50
The assistant referee signals for offside against Kieron Dyer. Free kick taken by David Forde.10:25
George Friend concedes a free kick for a foul on Nadjim Abdou. David Forde takes the direct free kick.7:51
Free kick awarded for an unfair challenge on Kieron Dyer by Karleigh Osborne. Direct free kick taken by Grant Leadbitter.5:20
Rhys Williams delivers the ball, comfortable save by David Forde. The ball is delivered by Nicky Bailey, comfortable save by David Forde.2:12
The referee blows for offside against John Marquis. Stephen McManus takes the free kick.1:09
Free kick awarded for an unfair challenge on Marvin Emnes by Alan Dunne. Free kick taken by George Friend.0:00
The game kicks-off.
Live data and text provided by our data suppliers