Manchester City's hopes of winning a fifth-straight Carabao Cup were ended as they fell to a 5-3 defeat on penalties at West Ham.
After a goalless 90 minutes of their last-16 clash at the London Stadium on Wednesday night, Phil Foden's missed penalty proved costly for City, while the Hammers scored all five of their attempts to reach the quarter-finals of the competition.
City had progressed through or won their last 21 ties in this competition, last being beaten by Manchester United in the fourth round in 2016 - Pep Guardiola's first season at the club. Their hopes of a record fifth win are over.
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But for West Ham, who themselves beat Man Utd in the previous round, a dream start to the campaign continues across all competitions for David Moyes and his men.
City crash out on penalties at the London Stadium
There were 17 changes made in all by both sides following on from their weekend Premier League games, and it largely showed in terms of the quality of the first half.
Both sides had one half chance as Mark Noble stung the palms of Zack Steffen with a shot from the edge of the area, and the goalkeeper was slightly fortunate that his weak parry fell to Fernandinho to clear rather than a lurking West Ham body. At the other end not long after Cole Palmer found space in the box to shoot for City, but Alphonse Areola was on hand to keep it out.
It was a much more open game in the second half, with Areola much more busy in the West Ham goal, making a string of saves including one brilliant stop on 58 minutes to keep out a John Stones header from near point-blank range.
Changes were made as both managers looked for a win before penalties, with Jarrod Bowen, Said Benrahma, Foden and Jack Grealish all being introduced in the closing stages.
Glorious opportunities presented themselves at both ends for the tie to be won in normal time, too. At one end it was Tomas Soucek who could only fire over, and with the last action of the game substitute Gabriel Jesus crossed to an unmarked Raheem Sterling, but he could only head straight into the arms of Areola.
And the West Ham goalkeeper did enough in the shootout to force Foden to put City's opening penalty wide, with West Ham netting all of theirs to progress to the quarter-finals of the Carabao Cup for the first time since 2018.
What the managers said...
West Ham's assistant manager Stuart Pearce: "The team showed so much resilience over 90 minutes. We missed a couple of decent chances and with the honesty of the team we deserved to get over the line. It was a really good night for this football club, with 60,000 in the stadium. It was absolutely superb.
"The players deserve all the credit, and credit to the manager as well. He drives this football club on on a daily basis. Anyone approaching 1,000 matches has to be taken very seriously, and he's done a wonderful job.
"We feel as though we're in a building process here. Hard work underpins everything we do here and we won't get washed away. There are big challenges ahead, but he's developing and growing this club."
Man City's Pep Guardiola: "An incredible run has finished. We finished in a good way. We played in a really good way, creating chances against a team who defended deep. On penalties, they were better. Congratulations to West Ham. Phil had the courage to be the first taker but unfortunately he missed it. The experience will help him next time.
"It was one of our toughest games against them. They are doing well in the Premier League, the Europa League and now they are into the quarter-finals of the Carabao Cup. They are a fantastic team with a fantastic manager. We played our game and sometimes this happens. When you get to penalties anything can happen. Next season we'll be back."
Man of the Match - Alphonse Areola
Not quite the shoot-out hero, with the only penalty that failed to go in being missed entirely by Foden, but there's every chance West Ham would not have even got to that point in the tie were it not for Areola, who made multiple crucial stops in the second half to keep the tie goalless. Simply too good to be a back-up goalkeeper in the Premier League, and the Hammers can consider themselves lucky to have him as their No 2 in that position.
When is the draw for the Carabao Cup quarter-finals?
The quarter-final draw will take place live on Soccer AM this Saturday from 10.30am
Hosts Fenners and Jimmy Bullard will be conducting the draw, which will be live on Sky Sports Main Event, Sky Sports Football, Soccer AM's YouTube channel and the EFL's Twitter account.
Carabao Cup 2021/22 schedule...
- Quarter-finals: December 21 and 22
- Semi-finals: January 4/5 and 11/12
- Final: February 27
What's next for West Ham and Man City?
West Ham travel to face Aston Villa in the Premier League on Super Sunday, live on Sky Sports Premier League and Main Event; coverage starts at 4pm with kick-off at 4.30pm. Manchester City host Crystal Palace on Saturday at 3pm.