Wayne Rooney, Michael Carrick and Ashley Young all missed their spot-kicks and the Championship team came away with a 1-3 victory to reach the quarter-finals of the competition.
So now here are all the best jokes as Manchester United are knocked out of the League Cup on penalties by Middlesbrough:
— Man United News (@ManUtdMEN) October 28, 2015
We shouldn't be subjected to extra time for this Man U – Boro game.
— Atuhaire J Sherura (@julzsherura) October 28, 2015
Lvg loves possession . Scoring a goal gives possession away. That is against the philosophy
— Man_Utd is life!!! (@Man_U_4everr) October 28, 2015
Carragher's predictions are as bad as United's penalties
— Andy (@AJ3Fifa) October 28, 2015
That'll be a loooong trip back down south for United fans
— Etihad Stadium (@Etihad_Stadium) October 28, 2015
Manchester United are OUT! pic.twitter.com/TQUdiVXx7j
— Football Funnys (@FootballFunnys) October 28, 2015
Cue United fans saying 'They're focusing on the league'
— Copa90 (@Copa90) October 28, 2015
Please MAN U fans I want to BORO money. If I don't pay I pay the Penalty!
— Gentleman (@daldino) October 28, 2015
@FootyAccums cue all Man U fans "it's a rubbish cup anyway"
— Sean Dresser (@seandresser) October 28, 2015
Jurgen Klopp reacting to news that Man U are knocked out by Boro at Old Trafford…………. https://t.co/eSCJCczA5a
— Kop End (@kopitetilldeath) October 28, 2015
Imagine earning 300k a week and not being able to hit an 8 ft by 12 ft rectangle with a round ball weighing 0.2 grams from 12 yards #mufc
— Ander™ (@Ahnaf_Rahman) October 28, 2015
Manchester United. pic.twitter.com/rMdKVVyX1b
— Footy Jokes (@Footy_Jokes) October 28, 2015
If a man steals 300k a week from a bank he's called a thief! If a man steals 300k a week from a football club he's called Wayne Rooney😤#mufc
— Mitch Clarke (@mitch5clarke) October 28, 2015
Man U fans dey form sleep….. Don't worry, we will remind you in the morning. Sweet dreams pic.twitter.com/MyPgExO0AO
— Adé O. 'SNC' (@StrictlyNaija) October 28, 2015
— Jade ♡ (@JadeStamate) October 28, 2015