Atalanta stunned Anfield as Gianluca Scamacca scored twice in a 3-0 win to leave Liverpool with a mountain to climb to reach the Europa League semi-finals.
Mario Pasalic added a third seven minutes from time to condemn Liverpool to a first home defeat in all competitions for 14 months.
“Nothing positive to say about the game,” said Jurgen Klopp.
“They [Atalanta] 100 per cent deserved it. It was a really bad game. I didn’t like our tactical discipline. We were everywhere. No counter press. I know the boys can play better football, but not tonight.”
The Reds had been favourites to end the Klopp era by completing the German’s set of trophies won as Liverpool boss in his last game in charge in the Dublin final.
With Liverpool locked in a tight three-way battle for the Premier League title alongside Arsenal and Manchester City, Klopp showed that remains his priority as he made six changes to the side that were held 2-2 by Manchester United on Sunday.
Mohamed Salah was one of those left on the bench but he was unable to inspire a response despite being thrust into action right at the start of the second half after a lacklustre first 45 minutes from the home side.
Atalanta had won just two of their previous nine games in all competitions. But the side sitting sixth in Serie A were a threat from the first whistle. Pasalic missed a glorious chance to open the scoring after just three minutes when he fired into Caoimhin Kelleher’s face as the Irish international spread himself.
Harvey Elliott hit the crossbar and Darwin Nunez sliced wide when clean through on goal but those promising Liverpool attacks were few and far between.
Scamacca failed to shine during his one season in the Premier League with West Ham, but he has now scored three times in England for club and country this season.
Atalanta made the breakthrough on 38 minutes when the Italian international fired low through Kelleher’s grasp from Davide Zappacosta’s cross.
Teun Koopmeiners should have made it 2-0 before the break when he failed to beat Kelleher one-on-one.
Klopp reacted at half-time as Salah, Dominik Szoboszlai and Andy Robertson were sent on in a rescue mission.
However, even the changes failed to muster a response from a jaded looking side in their 50th game of the season.
Scamacca was offered an acre of space to slot home Charles De Ketelaere’s cross on the hour mark.
Luis Diaz and Diogo Jota were then introduced by Klopp but Liverpool continued to create little despite their abundance of attacking talent on the field and left themselves open to the counter-attack.
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Atalanta took full advantage to close to within the brink of just their second ever European final.
Scamacca turned provider for the third after Szoboszlai gifted possession away inside his own half.
Ederson’s first effort was saved by Kelleher, but Pasalic thumped home the rebound to the delight of the travelling fans.
Liverpool have a history of thrilling comebacks in the European competition, most notably from 3-0 down at half-time in the 2005 Champions League final against AC Milan.
But they will need a fightback of that magnitude to keep alive the dream of sending Klopp out with a European trophy.
ADVANTAGE ROMA IN EUROPA LEAGUE DERBY WITH MILAN
Elsewhere, Gianluca Mancini gave Roma a slender advantage in their Europa League quarter-final with AC Milan after netting the only goal in a 1-0 win at the San Siro.
Just as in the weekend’s Rome derby in Serie A, Mancini headed home the winner from a Paulo Dybala corner to earn Roma a precious victory against their fellow Italians.
Mancini has had an eventful few days as he was fined 5,000 euros for waving a flag depicting Lazio supporters as rats in his post-derby celebrations.
The 27-year-old’s sixth goal of the season, in the 17th minute, gave his team a hard-fought victory and a lead to defend at next week’s second leg in Rome, when Roma will continue their bid for a third European final in as many years.
“I’m so happy. I’ve been spoken about a lot in the last few days but to win the derby and come here and win in the way we did, like a proper team, is a huge joy,” said Mancini to public broadcaster Rai.
“It’s a great night for us. I couldn’t have asked for more from this week.”
Friday’s win also continued former Italy midfielder Daniele De Rossi’s remarkable start as coach of his boyhood club who beat Milan at the San Siro for the first time since October 2017.
De Rossi has completely revitalised Roma since taking over from Jose Mourinho, who was dismissed in January after a league thumping at the hands of Milan.
Roma have only lost twice under his charge, to Italian champions-elect Inter Milan and Brighton in the previous round of the Europa League when that last-16 tie was decided in the first leg.
Milan, who struck the woodwork late on through Oliver Giroud, now face an uphill task to get something from their season as they trail Inter by 14 points in Serie A.
Stefano Pioli’s side, who came into Thursday’s clash on a run of seven straight wins, could even concede the league title to their local rivals in the next derby with Inter on Monday week, making next week’s return a huge fixture for the seven-time European champions.
LEVERKUSEN STRIKE LATE TO BEAT WEST HAM
Meanwhile, Jonas Hofmann and Victor Boniface scored after coming off the bench as Bayer Leverkusen beat West Ham 2-0 at home in their Europa League quarter-final first leg.
Needing stoppage time winners from Patrick Schick to win both legs of their last 16 tie with Qarabag, Leverkusen were dominant but had failed to break through against the dogged visitors.
With 14 minutes remaining, coach Xabi Alonso brought on Hofmann and Boniface and the move did the trick, the Nigerian linking with the Germany winger for the opener in the 83rd minute.
Boniface then sealed the result in stoppage time, heading in a Hofmann cross for a 2-0 win.
The victory continues what could be a stunning week for Leverkusen, who are 16 points clear of Bayern Munich in Germany and can win their first Bundesliga title by beating Werder Bremen at home on Sunday.
Alonso told reporters “the anticipation is huge — it couldn’t be bigger.”
“We have a chance on Sunday — if we win, we’re champions. We need to step on the gas and it would be something very special to achieve.”
“The fans singing gave me goosebumps,” Hofmann told German TV network RTL.
“It means everything to be able to hold up the shield at the end of the season. It will be a moment where maybe a few tears will fall. We might get overwhelmed, but you need to let your emotions flow.”
West Ham, who fought hard with little in the way of possession or field position, will need to become the first team to beat Alonso’s side this season to return to the semi-finals.
West Ham coach David Moyes praised his opponents.
“We’re playing a Champions League (level) team tonight — and a good one at that,” said Moyes.
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