Atalanta took home a comfortable yet valuable three points away from Liverpool after notching a 2-0 win at Anfield, meaning both the visitors and Ajax sit with seven points, just two behind Liverpool in Group D.
Jurgen Klopp made the call to rest several star players after making vocal his displeasure of this seasons congested fixture list over the weekend.
The decision looked to have backfired, with his men unable to make a breakthrough and seemingly allowed the visitors to grow into the tie.
Two close-range strikes from Josip Illicic and Robin Gosens in the second half sealed the deal and enabled Gian Piero Gasperini's side to shut-up shop for the games remainder.
This is the Warm Down of a disappointing night for the Reds, who missed out on what would have been the earliest progression to the knockout phases of the Champions League since 2006/07.
A 100% start in Europe and a tight fixture turnaround meant there was some leverage in the German's squad selection, after having 10 unavailable players at the weekend, or in his words, 'a few instruments missing out of orchestra'.
Mo Salah made his return after a negative coronavirus test and veteran James Milner played out his 50th appearance for Liverpool in Europe.
Young defender Rhys Williams became the first ever outfield Liverpool player to make four consecutive appearances all in the Champions League, returning from hip injury on international duty and partnering Joel Matip for tenth centre back pairing for the Reds this season.
The pair were flanked by young full backs Neco Williams and Kostas Tsimikas, while Divock Origi joined the usual suspects of Sadio Mane and Salah leading the line.
Slow out of the gates
The much changed starting eleven failed to make an instant impact, or any impact for that matter, in the first period of the game and lacked an incisive edge to their play.
Both sides were guilty of being too lax on the ball, but most notably Salah, Matip and Williams amongst those in red- Alisson was forced into a reactionary save from a stinging Gosens effort after Liverpool were caught in possession.
Liverpool had their moments to flex their defensive capabilities, most notably Curtis Jones regaining the ball in the middle of the park in wake of a solid performance against Leicester, and also Williams atoning for an earlier lapse of concentration with a well timed challenge on Gosens.
In front of goal, Klopp's men were blunt and at times static, with Origi and Salah not corresponding on the same wave length when trying to find each other on the counter.
The Reds eventually recorded their first effort through Salah firing over on his weaker right foot a minute from the break, concluding a half that was crying out for some Scottish and Portuguese influence from the bench.
All change- no difference?
The opening stages of the second half brought with it some glimmers of hope, James Milner of all players coordinating some quick football in the final third.
Loss of possession in midfield caused outrage from Jurgen Klopp and prompted the long awaited changes, four at once that included the Brazilian pair of Fabinho and Roberto Firmino, along with Andy Robertson and Diogo Jota.
While the would-be difference makers waited in the wings, Illicic stabbed home Atalanta's first of the night from an Alejandro Gomez cross; the latter afforded so much space by the Welsh right back that may have been an evening to forget for the youngster.
Even after the introduction of the first team regulars, Atalanta did not hang around and doubled their lead with composed build up play that was finished off by Gosens, receiving a well placed header from Hans Hateboar after the space in the Liverpool back line was exposed yet again.
Bar a few commendable examples of more direct football from the likes of Jota and Milner, there was hardly any progression in front of goal for the Redmen after Klopp's tactical switch up- pressure was truly mounding for the home outfit.
The story of the final 25 minutes was the solidity of Atalanta's men at the back.
Cristian Romero, on loan at the Bergamo side for two seasons, showcased his potential for Juventus in years to come, evident in his strong reading of the game and ability to get on the ground when needed at the age of 22.
Klopp's fifth and final roll of the dice saw Takumi Minamino take to the field in place of Joel Matip, with Fabinho back in his accustomed centre half position of late.
The all-out Liverpool attack seldom reaped the benefits of having four offensive minded players on the park, a real stark contrast to that of the 3-0 win over Leicester.
Hateboar was able to telegraph a misplaced pass and released Gomez onto what was an ultimately ill-fated counter attack, but the evidence was clear that the low block employed by Gasperini proved too much for Liverpool's aggressive approach in the game's last phases.
Multiple failed limp attempts to get the ball into the danger area by Fabinho and Williams were the last actions of a performance that was a stark contrast to that of three weeks ago when condemning Atalanta to their heaviest ever home European defeat on matchday three.
Still, time will tell whether or not the resting of key personnel will take effect against Brighton on Saturday lunchtime.