Wayne Rooney, Michael Carrick and Ashley Young all missed penalties as Middlesbrough knocked Manchester United out of the Capital One Cup on penalties at Old Trafford.
Boro goalkeeper Tomas Mejias saved from Rooney and Young, while Carrick blazed his effort over in between as Boro advanced to the quarter-finals with a 3-1 victory following a 0-0 draw after 120 minutes.
Louis van Gaal's side were lacklustre on the night against a side that took Liverpool to penalties in this competition last year and eliminated Manchester City in the FA Cup - and United were fortunate to survive past 90 minutes, with Daley Blind twice surviving own-goal scares.
He saw one wild hack into the net chalked off for an offside flag against Kike before he breathed a huge sigh of relief as Sergio Romero's mis-control from his back pass went narrowly wide.
Jesse Lingard struck a post in the 90th minute while Grant Leadbitter and Stewart Downing were denied by Romero in stoppage time.
The hosts should then have sealed their progress as they produced a spate of extra-time misses, Marouane Fellaini, twice, and substitute Anthony Martial guilty of missing close-range headers.
And Boro, losers of a 14-13 shoot-out epic at Anfield last season, made them pay on penalties as United joined Arsenal and Chelsea in crashing out at the last-16 stage.
The travelling contingent for this fixture stretched into five figures and they made their presence known vocally and visually by shining phone lights 10 minutes in as a show of solidarity for the job losses in the steel industry on Teesside.
They had cause to cheer when George Friend nutmegged Lingard and, moments later, the same player should have sent them in ecstasy. United failed to clear a corner from the left and Emilio Nsue's ambitious overhead kick fell straight into Friend's path, but the full-back placed his effort directly at Romero from six yards out.
For the hosts, the likes of Fellaini and Memphis Depay were doing little to prove they warranted consideration from Van Gaal in more high-profile fixtures, the latter in particular constantly losing possession with loose touches and firing a halfway line lob well over Mejias' net.
Van Gaal had clearly seen enough at the interval, taking off James Wilson for Rooney, and the hosts at least tested Mejias with a series of shots down his throat, one from Depay that he almost fumbled back over his line.
That error would have made a blooper DVD but the one from Blind 12 minutes into the second period deserved to grace a cover.
Kike was flagged offside when hitting an effort against Romero's far post and as the ball came back across the six-yard box, Blind somehow managed to slam the ball directly into the net with no one around him.
His head entered his hands but fortunately for him the linesman's flag spared his blushes.
The comedy of errors continued, though, as Romero allowed Blind's back pass to almost creep in at the back post in a manner reminiscent of ex-Aston Villa goalkeeper Peter Enckelman's howler against Birmingham.
That, coupled with Leadbitter's fierce shot at Romero, prompted Van Gaal to call for Martial too in place of the disappointing Depay with 19 minutes left.
The game was meandering towards extra-time until both sides came to life in the dying stages. Lingard, who hit the woodwork in the Manchester derby on Sunday, smashed an effort against a post before the visitors broke on the counter and Romero stood up to repel Leadbitter's lob and then Downing's drilled effort in stoppage time.
In extra time Fellaini was pushed in advance of Rooney and somehow failed to head in from close range on two occasions.
The hosts felt they should have been awarded a penalty when Martial flicked up onto Daniel Ayala's outstretched hand and the Frenchman could have prevented the flurry of spot-kicks that soon followed had he nodded in Lingard's head across in.
Rooney was the first to miss and although David Nugent blazed over, Carrick did likewise before Mejias guessed right again to deny Young and send Boro through.
TWEET OF THE MATCH
"Man Utd v Middlesbrough is one helluva game." - MEP Patrick O'Flynn (@oflynnmep)
PLAYER RATINGS
MAN UTD
Sergio Romero: 8
Marcos Rojo: 6
Memphis: 6
Chris Smalling: 6
Michael Carrick: 6
Daley Blind: 5
James Wilson: 6
Marouane Fellaini: 7
Jesse Lingard: 8
Matteo Darmian: 6
Andreas Pereira: 7
Substitutes
Wayne Rooney: 6
Ashley Young: 6
Anthony Martial: 7
MIDDLESBROUGH
Tomas Mejias: 9
George Friend: 8
Daniel Ayala: 6
Ben Gibson: 8
Grant Leadbitter: 8
Kike: 7
Carlos de Pena: 6
Jack Stephens: 6
Stewart Downing: 8
Emilo Nsue: 7
Tomas Kalas: 6
Substitutes
Bruno Zuculini: 6
David Nugent: 5
Adam Clayton: 6
STAR MAN
In a game of so many chances, anyone with the winning goal in normal time would have made the cut here. However, it was Middlesbrough goalkeeper Tomas Mejias who saved twice during the penalty shootout, first from Wayne Rooney and then from Ashley Young, which sealed victory for Boro. His presence in the match had already been enough to deter the many crossing attempts from United, which meant the visitors battled their way into the shootout.
MOMENT OF THE MATCH
One for the funniest home videos section perhaps, but Daley Blind ended up scoring a bizarre own goal with a tight-angle 'finish' Wayne Rooney would have been proud of. Boro's Kike struck the bar with a low, curling effort and Blind somehow managed to side foot the rebound past Sergio Romero. It was then ruled out for offside.
VIEW FROM THE BENCH
In some ways, Aitor Karanka and Louis van Gaal are very much alike. Both have the ability to remain in pretty much one stance throughout the match - that of quiet consideration. In the first half, Karanka, stood calmly near the touchline, had plenty of reason to be confident as his side kept United at bay and threatened to take the lead. Van Gaal in his usual seated position, would have taken heart from the second half. Van Gaal had already made all his substitutions even before Boro made their first. United were certainly boosted by their fresh arrivals, though Karanka's faith in Boro's stamina was eventually rewarded. His final sub came in minute 114 and Boro slogged their way into the fifth round.
MOAN OF THE MATCH
The game was set up for Memphis Depay to re-announce himself at Old Trafford. The Dutchman had seemingly fallen down the pecking order prior to the game - not least with the rise of Jesse Lingard - and had been reduced to substitute performances in recent weeks. On Wednesday night, Memphis was reduced to chasing the ball often and his passes were largely erroneous. Even when he did get half-chances they were squandered. A sign perhaps of the weight the number seven shirt is putting on him at Manchester United, who were left almost carrying him until he was replaced on 71 minutes by Anthony Martial.
WHO'S UP NEXT?
Crystal Palace v Manchester United (Barclays Premier League, Saturday October 31)
Middlesbrough v Charlton (Sky Bet Championship, Saturday October 31)
Source: PA
