Liverpool succumbed to a shock 3-0 Europa League quarter final defeat to Serie A outfit Atalanta courtesy of a Gianluca Scamacca brace, and a late goal from Mario Pasalic.
The Reds almost took the lead when a fierce curling effort from Harvey Elliott on 25 minutes struck both the crossbar and the post.
But Atalanta put their noses in front when former West Ham striker Scamacca fired home from Davide Zappacosta’s cross.
Reds keeper Caoimhin Kelleher got hands to Scamacca’s effort, but could not deny the visitors from taking a 1-0 lead as it squirmed under his body.
Scamacca doubled the visitors’ lead on the hour mark as he expertly steered home a well crafted cross from Charles De Ketelaere, who was a constant dangerman.
Teun Koopmeiners could have buried the first leg of the tie when he was played in behind by De Ketelaere, but the Dutchman could only fire his effort wide from a tight angle.
Jurgen Klopp‘s men tried to claw themselves back into the game, as Joe Gomez fired long-range efforts both over the bar and wide of the post.
Mo Salah thought he had scored from Andy Robertson’s cross on 78 minutes, but his effort was denied by an offside flag.
And to make matters worse Gian Piero Gasperoni’s side took the spoils at Anfield when Pasalic scored from a rebound to give his side a 3-0 advantage.
Klopp and Co have given themselves a mountain to climb in the second leg which takes place in Bergamo next Thursday.
They will have to replicate their historic European comeback efforts of previous years to book their place in this season’s Europa League semi-finals.