A much-changed Liverpool finished top of the Champions League group phase despite losing their 100% winning record after defeat to PSV Eindhoven in a five-goal thriller.
Liverpool, who had won their opening seven matches, led twice in the Netherlands before conceding twice at the end of the first half in their eighth and final game.
But Barcelona's failure to beat Atalanta meant Arne Slot's team finished top on 21 points, two ahead of their nearest rivals.
In an action-packed first half, Cody Gakpo put the Reds ahead from the penalty spot in his home city against his former club after Joey Veerman had fouled by Federico Chiesa.
Johan Bakayoko equalised after a lovely turn and finish, before Harvey Elliott restored Liverpool's lead after Chiesa's attempt had been parried into his path.
But goals by Ismael Saibari and Ricardo Pepi condemned the current Premier League leaders to their first defeat in Europe this season.
Liverpool finished the match with 10 men after substitute Amara Nallo was shown a straight red card for an 87th minute foul on Bakayoko.
With the Reds already guaranteed a place in the last 16, Slot rested many of his first-team players before Saturday's crucial Premier League game at Bournemouth.
And the Dutchman suffered just his third defeat in his 35th game in charge of Liverpool as Dutch League leaders PSV finished 14th in the 36-team table to clinch a play-off place.
Liverpool's last-16 opponents will be the winners of a play-off involving Paris St-Germain, Benfica, Monaco and Brest.
Reds rest stars as Nallo dismissed on debut
Despite defeat, Liverpool finish top of the group phase and can now concentrate on domestic matters - where they are top of the Premier League, in the semi-finals of the EFL Cup and the FA Cup fourth round - before their next European game in March.
With Liverpool and Barcelona finishing first and second respectively, the two clubs cannot meet until the final.
Mohamed Salah, captain Virgil van Dijk and Trent Alexander-Arnold were among those given the night off as Jayden Danns became the youngest player ever to make his first start for Liverpool in a European Cup/Champions League game at the age of 19 years and 13 days.
Danns was one of four players aged 21 or younger to start while Trey Nyoni, 17, and Nallo, 18, came on as substitutes.
Nallo will not forget his senior debut in a hurry.
He lasted three minutes and 46 seconds, with the young defender managing just two passes before he was sent off.
"It is cruel but he has never played first team football before and to make your debut in the Champions League is probably the hardest," said Slot.
"A career isn't always positive, it also has negatives and he has to make sure he plays in this competition again."
Despite the result and Nallo's red card, Liverpool march on and are sure to wheel out their main players when they next play in the competition in the first week of March.
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