Liverpool still require one more win to reach the Champions League last 16 after they were beaten 2-0 by Atalanta at Anfield.
The Serie A club were mature and methodical as they avenged the 5-0 defeat in the reverse fixture earlier this month, and were good value for their victory as Liverpool registered no shots on target during the entire match.
Josip Ilicic broke the deadlock from Papu Gomez's cross on the hour-mark before Robin Gosens doubled their lead (64) as Liverpool suffered an off night.
The result means the Premier League champions remain top of Group D on nine points but Ajax joined Atalanta behind them on seven points each after their 3-1 win over Midtjylland, which eliminated the Danes.
Liverpool: Alisson (6), Neco Williams (6), Matip (6), Rhys Williams (5), Tsimikas (5), Milner (6), Jones (5), Wijnaldum (5), Salah (5), Origi (4), Mane (6).
Subs: Fabinho (6), Firmino (6), Minamino (n/a), Jota (6), Robertson (6).
Atalanta: Gollini (6), Toloi (7), Romero (8), Djimsiti (7), Hateboer (7), de Roon (7), Freuler (7), Pessina (7), Gosens (8), Gomez (9), Ilicic (7).
Subs: Mojica (6) Miranchuk (n/a), Zapata (6).
Man of the match: Papu Gomez.
Mature Atalanta punish passive Reds
Nothing that happened on the pitch at Anfield would eclipse the news which broke hours before this contest, with Diego Maradona's passing rightly set to dominate the media in the coming days, and a minute's silence was held before kick-off to honour the Argentina legend.
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Liverpool knew that victory would assure their place in the last 16 when the competition returns in February, but it took them 44 minutes to produce their first shot. James Milner played a free-kick short to Kostas Tsimikas, and after Rafael Toloi failed to properly clear, Mohamed Salah's right-foot effort failed to trouble Pierluigi Gollini.
Atalanta were by far the more threatening as Gian Piero Gasperini watched his side play the more enterprising football, orchestrated by the evergreen Gomez.
Mohamed Salah returned to Liverpool's starting line-up after his recent positive Covid-19 test as manager Jurgen Klopp made five changes for the Champions League visit of Atalanta. Klopp named a second-string defence with only Joel Matip remaining from Sunday's win over Leicester as Neco Williams, Rhys Williams and Kostas Tsimikas all came in to start.
James Milner moved from right-back to midfield with Salah and Divock Origi coming in up front. Atalanta made six changes from their 5-0 defeat to the Reds three weeks ago, strengthened by the inclusion of the likes of Robin Gosens and Marten De Roon.
The Argentine was once defended by Maradona for a foul on Lucas Biglia during a Serie A clash which placed the-then AC Milan midfielder's presence at the 2018 World Cup in jeopardy, and his sharp turn of pace and low centre of gravity lit up a drab opening 45 minutes.
Atalanta carved out the best chance as Cristian Romero found the overlapping run of Robin Gosens but his snapshot was palmed away at his near post by Alisson. There was one other noteworthy incident when Ilicic fell theatrically under a challenge from Tsimikas but referee Carlos Del Cerro Grande was unmoved.
Having won their first three games without conceding a goal, Liverpool knew they had done the hard work already - but Jurgen Klopp was unimpressed, seeking to inject some much-needed urgency into his troops at the break.
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The Liverpool manager sent out Diogo Jota, Andrew Robertson, Fabinho and Roberto Firmino to warm up within minutes of the restart having seen little improvement, but worse was to come as Atalanta duly took the lead.
Inevitably, Gomez was involved as his sublime cross from the left was stabbed home from close range by Ilicic, underneath the body of Alisson.
2 - Liverpool lost a competitive home match by a margin of more than one goal for the first time in 137 matches at Anfield under Jürgen Klopp, with this their heaviest such defeat since August 2015 in the Premier League against West Ham under Brendan Rodgers (0-3). Anomaly. pic.twitter.com/78YKokJE9A— OptaJoe (@OptaJoe) November 25, 2020
Four substitutes and four minutes later, Liverpool were 2-0 down. Another cross from Gomez was this time headed back across goal by Hateboer and Gosens was unmarked to volley in from seven yards out.
This was unfamiliar territory for the six-time European champions. Indeed, it was the first time Liverpool had been two goals behind in a Champions League game at Anfield since October 2014, against Real Madrid.
The hosts were playing the price for their passive display, with news of Ajax's lead over Midtjylland putting the squeeze on their advantage at the summit - but there would be no historic comeback this time.
Duvan Zapata blazed a late chance of a third over but having dismantled Atalanta in Bergamo three weeks ago, this was a rude awakening for Liverpool ahead of the visit of Ajax next week.
What the manager said
Liverpool boss Jurgen Klopp told BT Sport: "It was not a good game. From both teams, didn't create a lot, until they scored the goals.
"A deserved defeat in a difficult game. The ref didn't whistle a lot and that makes it even more difficult, for both sides. It was unbelievably intense and you need some breaks.
"When the first half is gone, you usually settle but for some players who didn't play for a while it was very intense for them. We didn't find a way in the game.
"Easier to talk about a good game. We had moments but not real chances. It could happen to other teams. Thumbs up, no injuries and we go again."
Analysis: Fringe players fail to take opportunity
Former Liverpool striker Neil Mellor told Sky Sports:
"The priority was the weekend against Brighton because of how strong a position Liverpool already find themselves in. Ultimately, it's about getting through the group. Liverpool ideally would like to win the group, but there's two games still to go - one at home to Ajax while they'd be expected to win the final game if it does go down to it against Midtjylland.
"Klopp made the five changes tonight, and it was flat, it was disjointed. The lads who came in didn't take their opportunity. It's a reminder that Atalanta are a decent side and they responded to the defeat a few weeks ago. They didn't give Liverpool the space they did in that first game and got their rewards."
Man of the match - Papu Gomez
Salah was back after a couple of negative Covid tests, but he was overshadowed by the brilliant Gomez. No player produced more passes in the opposition's half than the 32-year-old (44), who enjoyed his evening back on Merseyside, providing an assist as well as playing a role in the build-up to the second.
It was three years ago this week that he laid on two assists during Atalanta's 5-1 thrashing of Everton in the Europa League, and on the night when Maradona's career has been celebrated, it only seemed fitting that his countryman in a No 10 shirt would leave such an impression on the pitch.
Shot-shy Liverpool - Opta stats
- Liverpool lost a competitive home match by a margin of more than one goal for the first time in 137 matches at Anfield under Jürgen Klopp, with this their heaviest such defeat since August 2015 in the Premier League against West Ham under Brendan Rodgers (0-3).
- Atalanta have won each of their last four away games in the UEFA Champions League, scoring 13 goals in the process and keeping a clean sheet in three of those four wins.
- Each of the last three sides to win their first ever away game against Liverpool in all competitions have been Italian clubs (Fiorentina in December 2009, Udinese in October 2012, Atalanta today). Indeed, Atalanta are the first side to win their first ever such visit to Anfield by more than one goal since Spartak Moscow in November 1992 (also 2-0).
- For the first time since Opta began recording shot data in the Champions League in 2003-04, Liverpool failed to attempt a single shot on target in a home game in the competition.
Liverpool travel to face Brighton at the Amex Stadium on Saturday in the Premier League; kick-off 12.30pm. They return to Champions League action when they host Ajax on Tuesday, December 1; kick-off 8pm.