Manchester United would be disappointed with the shock loss to giant killers Bristol City in the Carabao Cup quarterfinal. Jose Mourinho’s side lifted the title last year and it was another silverware hope this term. However, they could not overcome the Championship side despite having key figures in the encounter. Well, there have been numerous cup upsets for Manchester United.

Back in 2011, Crystal Palace defeated United in the League Cup quarterfinals. Second half sub Darren Ambrose opened scoring but Federico Macheda restored parity few minutes later. Glen Murray won it in extra time as he bundled home Ambrose’s free kick.

A year before that Leeds sent United packing in the FA Cup third round. Sir Alex Ferguson’s side could not prevail over Leeds even with Wayne Rooney, Dimitar Berbatov, Danny Welbeck and Gary Neville starting the game. Jermaine Beckford scored in the 19th minute and the team held on to that sole goal until the end to deny United.

In 2014, MK Dons delivered a shocker as they defeated the Red Devils 4-0 in the second round of the League Cup. United had Welbeck, Javier ‘Chicharito’ Hernandez, David De Gea, Shinji Kagawa and others in the lineup yet they were humbled by the Dons. Coach Louis Van Gaal was shocked at the happenings as Dele Alli inspired his side to the victory over United.

Middlesbrough also delivered a recent shock when it 2015 they defeated United in the League Cup round four. Van Gaal was also in charge as Aitor Karanka’s men shocked their hosts. Memphis Depay, Michael Carrick, Marouane Fellaini, Jesse Lingard and Sergio Romero made the team and even when Anthony Martial, Ashley Young and Rooney came on, they could not stop the loss through penalty shootout.