Manchester United were dumped out of the League Cup on Wednesday after losing on penalties to second-tier Middlesbrough who reached the quarter-finals having withstood a late onslaught to secure a 0-0 draw in extra time.
Middlesbrough, who are coached by Spaniard Aitor Karanka, were clinical in the shootout as hosts United faltered with England internationals Wayne Rooney, Michael Carrick and Ashley Young all failing to convert from the spot at Old Trafford.
It was a much better night for two of United's fiercest rivals, new coach Juergen Klopp tasting victory for the first time as Liverpool beat Bournemouth 1-0 while Manchester City thrashed Crystal Palace 5-1.
Goals have been a priceless commodity for Liverpool this season and it was another nervy night as they scored in the first half through Nathaniel Clyne but could not add to their tally and were forced to hang on for the win.
Goals are rarely in short supply at the Etihad Stadium and City were ruthless as they brushed aside Palace with efforts from Wilfried Bony, Kevin de Bruyne, Kelechi Iheanacho, Yaya Toure (penalty) and Manu Garcia.
There was more woe for managerless Aston Villa who lost 2-1 at Southampton. Maya Yoshida and Graziano Pelle put the hosts two goals up before Scott Sinclair netted a late consolation from the penalty spot.
United became the latest high-profile casualty in the fourth round after Tuesday night saw Arsenal knocked out by second-tier Sheffield Wednesday and Chelsea beaten by Stoke City.
Middlesbrough thought they had scored in the second half when Daley Blind slammed the ball into his own net, only for an offside decision against Kike sparing the Dutchman's blushes.
United should then have wrapped up the contest in extra time but striker Anthony Martial and midfielder Marouane Fellaini missed fantastic chances to head them in front.
"It's very disappointing," coach Louis van Gaal told reporters. "We have to solve this problem, we have to finish our chances.
"I'm pleased with some performances of my players but I am also disappointed with some of my players. That's the life of a manager."
SMILING KLOPP
Klopp was facing the prospect of going a fourth game without a win since taking over at Liverpool three weeks ago.
Three successive draws had dampened some of the euphoria around his appointment and a number of injuries to first-team players had limited his options, especially in attack.
The German picked a youthful and much-changed side to face Bournemouth but the match had a familiar feel to it as Liverpool dominated possession and failed to carve out clear-cut chances.
The only goal came in the 17th minute when the impressive Roberto Firmino released Joao Carlos Teixeira. His backheel was cleared off the line only for Clyne to follow up and sweep the ball home.
"My first win feels better than a draw," said a smiling Klopp. "We were dominant and got the win we deserved.
"It was very important to win because we decided to go with a new team. To win is always good for the feeling of the whole team."
While City drew a blank at Old Trafford in the Manchester derby on Sunday, they reverted to type against Palace as they scored five goals or more for the third time this month.
The home team took the lead when Bony powered home a header from a corner after 22 minutes before Belgium's De Bruyne continued his excellent form by lashing the ball home at the far post a minute before halftime.
De Bruyne then set up youngster Iheanacho to make it 3-0 with an excellent goal 14 minutes after the break and Toure added his name to the scoresheet after Damien Delaney was penalised for holding at a corner.
Delaney grabbed a consolation headed goal but Palace's misery was rounded off when youngster Garcia ended a counter attack with a clinical finish.
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