After a goalless, but entertaining 90 minutes in which Pep Guardiola’s men were superior, the Hammers prevailed on spot-kicks after Phil Foden dragged his opening effort wide of the right post.

David Moyes’ side held their nerve to successfully convert all five of their attempts to seal a 5-3 shootout victory, as City lost a League Cup tie for the first time since October 2016.

Both teams played their part in an absorbing, keenly contested affair and, whilst both had opportunities to win the game in normal time, it was the visitors who created the majority of the chances at the London Stadium.

City’s best opportunity fell to John Stones, whose six-yard header from a Riyad Mahrezfree-kick was superbly saved by the impressive Alphonse Areola, whilst at the other end, Oleksandr Zinchenko, made a crucial block to deny Andriy Yarmolenko after Steffen had beaten away Arthur Masuaku’s fierce drive.

Stones effort was one of 25 chances City unleashed on the Hammers’ goal.

After a slow start, the game burst into life midway through the first half following Mark Noble’s fizzing 20-yard drive, which stung the palms of Steffen, but that was as good as it got for the hosts in the opening 45 minutes.

City saw several opportunities go begging.

Areola stuck out a leg to keep out Cole Palmer’s angled drive and Mahrez flashed a first-time volley across the face of goal from a tight angle, but the best opportunity fell to Nathan Ake, who rose highest from a free-kick but glanced his header wide of the post from six-yards.

Both teams upped the ante after the break and traded chances in a game which was anything but a boring stalemate.

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cute through ball put Gundogan in on goal, but he dragged across the face before Areola denied Raheem Sterling and Kevin De Bruyne in quick succession.

The Hammers’ goalkeeper got down smartly to keep out the winger’s low drive and adjusted well to save the Belgian’s deflected strike from the edge of the area.

Yarmolenko’s blocked shot was the best of the Hammers’ chances as Moyes’ men began to show more attacking intent.

Masuaku drilled over the bar from an acute angle before Aaron Cresswell and Nikola Vlasic combined to create an opportunity for Tomas Soucek, but the Czech midfielder sent his effort wide from 15-yards.

As penalties loomed large, there was a heart in mouth moment as substitute Foden’s deflected shot dropped into the unmarked Gundogan’s path inside the six-yard box, but the German was caught unaware and Areola gobbled up the loose ball.

The 28-year-old proved to be City’s nemesis and as the game became increasingly stretched, he stuck out a strong hand to tip a stinging 25-yard effort from Zinchenko over the bar.

In the shootout, Joao Cancelo, Gabriel Jesusand Jack Grealish all scored for City, whilst Steffen got a hand to Jarrod Bowen’s effort and did the same with Said Benrahma’s decisive spot-kick, but both had too much pace on them as the Hammers progressed to the quarter-final.