Kepa Arrizabalaga missed a sudden death penalty as Liverpool secured the Carabao Cup after a shootout that went all the way down to the goalkeepers.
The Spaniard had been brought on late in extra time as Thomas Tuchel turned to his spot-kick specialist with the score goalless after 120 minutes.
It was a cruel end for Chelsea and Kepa after a thrilling contest that saw the European champions waste three golden chances to take the lead in normal time.
Liverpool had a host of opportunities too after controlling long periods of play and thought a Joel Matip header had handed them victory only for VAR to rule it out. Later, a fractional offside denied Romelu Lukaku an extra time winner.
Kepa had been the shoot-out hero in the European Super Cup at the start of the season and could consider himself unfortunate to be left out of the starting line-up at Wembley.
First choice Edouard Mendy was picked instead, despite playing in none of the rounds leading up to the final. The Senegal international more than justified his inclusion with a series of saves, including a stunning double stop in the first half. But as the unofficial ‘cup keeper’ Kepa’s credentials were clear.
Still, he got his chance to be the hero once more and seemed destined to fulfil that role when brought on with just moments remaining in stoppage time.
He has proven himself an outstanding keeper in shootouts – but was unable to stop any of Liverpool’s 10 spot kicks from their outfield players. The closest he came to reaching one was when getting a hand to Ibrahima Konate’s effort, which was Liverpool’s 10th penalty.
It was then down to the keepers and when Caoimhin Kelleher fired past Kepa, it was down to the Chelsea man to keep the contest going.
But shooting into the Liverpool end of the ground with a backdrop deafening boos, he lifted his shot high into the stand behind the goal, leading to frenzied cheers.
Chelsea’s players immediately ran to console their teammate, but it was a bitterly painful moment for the 27-year-old.
It was also a second Wembley defeat for Tuchel after losing last year’s FA Cup Final to Leicester – and ends Chelsea’s hopes of a clean sweep in cup competition. This was the chance to win a third trophy this season after the Super Cup and Club World Cup.
But it was Liverpool’s day – even if a tense contest suggested the teams are a lot closer than the Premier League table would suggest.
This is the fourth time Tuchel and Jurgen Klopp have faced each other in England and the Liverpool manager is yet to win in normal time, having lost one and drawn two of the previous three.
Both teams will have felt they did enough to win it, with marginal offsides and some brilliant goalkeeping denying.
Chelsea should have been in front inside five minutes when Cesar Azpilicueta’s cross found Christian Pulisic free in front of goal. But the American’s finish was straight at Kelleher, who parried.
Then it was Mendy who produced a spectacular double save on the half-hour mark to deny Liverpool as they seized control of the game.
First he was down low to block Naby Keita’s shot from the edge of the area. But the powerful effort was too hot and handle and rebounded into the path of Sadio Mane inside the six-yard box.
With the goal beckoning Mendy sprung himself in front of the Liverpool striker to push the shot over the bar.
For long periods it was all Chelsea could do to hoof the ball clear from their own box, with no one to hold it up and relieve the pressure.
N’Golo Kante and Mateo Kovacic were overrun in midfield during that period, with no link-up play with the forwards.
Yet Liverpool created little by way of clear-cut chances before half time, while Chelsea should have gone in ahead when Mason Mount was picked out by Kai Havertz just yards from goal and fired wide.
The same player was guilty of wasting another golden chance at the start of the second half when put clean through on goal by Pulisic. But with only Kelleher to beat, Mount’s side-footed effort struck the post, prompting Tuchel to drop to his knees and beat the ground in frustration.
Salah burst through on goal on 64 minutes after Liverpool seized on a poor clearance from Mendy.
The Egyptian lifted his shot over Chelsea’s keeper, but before it could cross the line, the outstanding Thiago Silva had raced back to clear.
Liverpool looked like they were ahead two minutes later through Matip – but Virgil van Dijk was judged offside in the build up after referee Stuart Atwell was invited to review the incident at pitch side.
With Liverpool back on top Tuchel called for Lukaku and Timo Werner from the bench.
Yet it was Luis Diaz who was next to come close – running free on the left, his low shot on the angle was blocked by Mendy’s legs.
A huge goal-mouth scramble in the final 10 minutes saw Mendy again produce a fine reaction save, while Chelsea just about managed to clear the danger.
He pulled off another stunning save in injury time – pushing away Van Dijk’s powerful header that was destined for the bottom corner.
Lukaku then had the chance to prove the hero himself with a smart near-post flick from a Marcos Alonso cross that Kelleher managed to block.
Chelsea had the ball in the net in each period of extra time – first through Lukaku and then Havertz – but on both occasions the offside flag was raised.
Lukaku was particularly unfortunate with replays showing his arm had fractionally strayed beyond the last man.
With still no goal during extra time, it was down to penalties to decide it, with Tuchel bringing shoot out specialist Kepa in the final moments.
It proved a decisive moment – but not in the way Tuchel or Chelsea anticipated.
