Liverpool fell to a surprise 2-0 defeat against Atalanta on a night they were favourites to seal progression to the Champions League knockout stages.
Liverpool 0-2 Atalanta
• 0-1: Josep Ilicic (60')
• 0-2: Robin Gosens (64')
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Victory would have seen Liverpool clinch their place in the round of 16 with two games to spare, but it was an uncharacteristic display from the Reds as they failed to get going all night.
Two quick-fire goals by Josep Ilicic and Robin Gosens gave the visitors three points, meaning the Reds need a win against Ajax or Midtjylland to qualify to the next stage.
Image: Liverpool FC via Getty Images
It was an inexperienced back-line for the Reds, with Neco Williams and Rhys Williams both starting and Kostas Tsimikas replacing Andy Robertson at left-back.
Liverpool made a slow start to the game whilst the visitors gave a much better account of themselves in comparison to their showing three weeks ago.
The absence of Robertson and Trent Alexander-Arnold was evident, with the Reds struggling to pick up the pace and create any chances.
Atalanta looked more accomplished of the two sides as they attacked well down the Reds' right, but the final ball was often lacking for the Serie A side.
The first half was devoid of any real action as Liverpool failed to conjure up a shot on target, with a couple of Reds players catching Jurgen Klopp's glare for poor decision-making.
Image: Liverpool FC via Getty Images
Alisson, who had made a good block early in the first half, made another valuable contribution at the start of the second as he came out and collected well after Atalanta looked to have found a ball in behind.
Liverpool continued to look lacklustre and found themselves behind just before the hour mark as Josep Ilicic met Papu Gomez's cross and found the back of the net from close-range.
A frustrated Jurgen Klopp made a quadruple substitution after the goal, with Tsimikas, Wijnaldum, Divock Origi and Mohamed Salah all coming off.
Robertson, Fabinho, Diogo Jota and Roberto Firmino all came on in one fell swoop, giving the Reds a brand-new dimension.
But Atalanta found a second just minutes later as Matteo Pessina beat Robertson in the air and found Robin Gosens, who neatly tucked the ball past Alisson - leaving the Reds with everything to do in the final 25 minutes.
The changes had no real effect for Liverpool, who continued to look off the pace, with Atalanta denying the Reds from creating any chances.
Takumi Minamino came on for the closing stages as Klopp further tweaked his system, but it wasn't to be as Liverpool suffered a rare Anfield defeat in the Champions League.
While Liverpool see their advantage in Group D slashed to just two points, qualification is still in their hands, with a win against Ajax next week or Midtjylland on matchday six enough to secure their place in the round of 16.
But ultimately, it was a disappointing night for Klopp and co, who could have wrapped things up tonight and rested players in the final two fixtures.
Next up for the Reds is a trip to Brighton on Saturday, before an all-important clash against Ajax next week.
Liverpool XI: Alisson, N. Williams, R. Williams, Matip, Tsimikas, Milner, Wijnaldum, Jones, Mane, Origi, Salah.
LFC Globe's MOTM: Alisson
Next Fixture: Brighton (A) - 28 Nov, 12.30pm
