Mohamed Salah eclipsed Steven Gerrard as Liverpool's top scorer in the Champions League with his double record-breaking goal in a 1-1 draw against Midtjylland.
The Egypt international struck after just 55 seconds as his 22nd goal in the competition also proved to be the club's fastest.
However, Alexander Scholz's VAR-awarded 62nd-minute penalty denied Jurgen Klopp's side victory and their best return from the group stage.
The game was not the best advert for video technology with long delays over three second-half goal incidents which contributed to eight minutes of added time and plenty of additional frustration.
Klopp may have named Liverpool's youngest Champions League starting XI with an average age of just 24 years and 26 days but it would have been considerably lower had it not been for the surprise inclusion of Salah (28) and Fabinho (27).
In a dead rubber it seemed reckless to risk injury to two key men but there was method in Klopp's motive as the only three players who featured in Sunday's victory over Wolves – Salah, Fabinho and rookie goalkeeper Caoimhin Kelleher – all played a significant part.
Salah's early opener came courtesy of a mistake from Midtjylland, who became the first side to concede two first-minute Champions League goals in the same season.
Scholz's attempted backpass got stuck under the feet of centre-back Dion Cools and was seized upon by Salah who raced clear to trickle a shot past the goalkeeper.
Fabinho's major contribution came in the 33rd minute when he hooked Sory Kaba's header off the goal line, the second time he had made such a clearance having done similar in their opening fixture against Ajax.
And on the stroke of half-time Kelleher stood up strong to block Awer Mabil's close-range drive, producing an even better save from Erik Sviatchenko in the last five minutes.
Diogo Jota and Naby Keita both had good chances saved by Jesper Hansen but in another disappointing showing Divock Origi missed the target with only the goalkeeper to beat having been teed up by Salah when he could have gone it alone in a two-on-one.
Aside from Salah's goal it was a night of landmarks with 22-year-old Scouser Trent Alexander-Arnold becoming the club's third-youngest captain and their youngest in Europe.
By comparison Gerrard was 23 when he took the armband, although that was on a permanent basis.
Another academy graduate Leighton Clarkson, who Klopp described as one of the biggest talents in the club, made his European debut having previously only featured in two domestic cup ties last season.
Another bow came at the start of the second half when the highly-rated centre-back Billy Koumetio replaced Fabinho, becoming Liverpool's youngest player in the European Cup/Champions League at the age of 18 and 25 days.
Slotting in alongside Rhys Williams, Liverpool's central defensive partnership now had a combined age of 37 and Midtjylland almost took advantage of that inexperience with Evander smashing a shot against the crossbar.
With Kostas Tsimikas off the pitch receiving treatment, Midtjylland equalised in controversial circumstances.
Anders Dreyer was brought down by Kelleher but referee Francois Letexier spotted an offside flag and blew for the free-kick.
However, a VAR review advised the official to go to the pitchside monitor and the Frenchman subsequently awarded a spot-kick from which Scholz scored.
Scholz had a second goal ruled out for a legitimate offside flag as the arrival of Andy Robertson, Jordan Henderson and Roberto Firmino failed to get the game back under the Reds' control.
Liverpool's players, somewhat understandably, spent the last 10 minutes trying to avoid over-exertion or injury which only encouraged their hosts with Kelleher and then Henderson, with a sliding block on Evander after a breakaway, denying them a winner.
There was still time for Takumi Minamino to have a goal ruled out for a Sadio Mane handball as VAR continued to confound and confuse.
