Manchester United are out of the Capital One Cup after a shock fourth-round defeat to Middlesbrough on penalties.

After a frustrating 120 minutes of stalemate, the Reds scored only one spot-kick, through Andreas Pereira, as the Championship side claimed a famous scalp by winning 3-1 in the shoot-out.

United manager Louis van Gaal made nine changes to the side that started the 0-0 draw in the Manchester derby with Pereira, Jesse Lingard and James Wilson all afforded an opportunity to impress. Despite the youthful exuberance in the team, it was a rather flat opening period illuminated, literally, by the away fans’ protest against the proposed closure of the Redcar steelworks by lighting up their mobile phones.

Lingard and Memphis Depay swapped flanks in a bid to unsettle the Teessiders’ well-organised defence but the first save came at the other end when Sergio Romero kept out George Friend’s unconvincing effort following a scramble in the box.

Memphis attempted a speculative long-range poke that Tomas Mejias watched sail wide and the Boro keeper got behind Wilson’s shot soon afterwards, when Memphis and Marouane Fellaini did well in the build-up. Kike showed magnificent control but fired tamely at Romero while Friend blocked a Fellaini drive after the Belgian brought a high ball down in a dangerous position.

The best effort came late in the half when Stewart Downing’s left-footed rocket brought the best out of Romero, who dived to make a spectacular save. Wilson was limping on his way to the tunnel and he failed to reappear, with skipper Wayne Rooney taking his place.

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