Liverpool suffered a shocking 3-0 loss to Atalanta to compound a miserable week for the Reds following the 2-2 draw with Manchester United during the weekend.
Liverpool came into the tie confident – so much so that manager Jurgen Klopp decided to rest Mohamed Salah, Luis Diaz, Dominik Szoboszlai, and Andy Robertson.
However, that decision came back to hunt the German coach as a spirited Atalanta side grabbed a shocking 3-0 win at Anfield.
Italian international Gianluca Scamacca was at the double. He fired in a cross from Davide Zappacosta, which squirmed under the surprisingly buttery arms of Caoimhin Kelleher on 38 for the opener.
Scamacca completed his brace in the second half, somehow finding space behind the Liverpool backline before expertly arrowing in a Charles De Ketelaere cross with his weaker foot.
Kelleher made a great save in the early minutes and had to deny Teun Koopmeiners again before the half-time break.
Darwin Nunez had an early chance that he squandered, and Harvey Elliott hit the underside of the bar before La Dea took the lead.
Several Liverpool stars like Kostas Tsimikas and Kelleher (despite the many saves) were far from their best today.
Nunez skied another terrific chance to bring Liverpool back into the tie with the game at 1-0.
Szoboszlai made a dreadful mistake that allowed former Chelsea man Mario Pasalic to score the third and wrap up the win for the Serie A side.
Liverpool have a massive mountain to climb when they travel to Italy next week for the second leg.
Klopp will be wondering what he must do to turn the tide after two poor results. The draw to Manchester United set Liverpool back in the title race, even though all hope is not lost.
However, this loss leaves a bitter taste. The boys struggled to get going and were played off the park by an Atalanta side that wanted it more.