Academy graduate Jarell Quansah was denied a dream first goal by VAR in the final minute of added time as Liverpool squandered the chance to secure qualification for the Europa League knockout stage with a 3-2 defeat in Toulouse.
The 20-year-old, replacing ill captain Virgil van Dijk in the side, poked home in the seventh additional minute to claim what would have been a barely-deserved point in southern France.
However, VAR alerted referee Georgi Kabakov to a potential handball after the ball bounced up off Alexis Mac Allister’s chest in the build-up and the Georgian official contentiously chalked it off.
Even a draw would have hardly papered over the individual errors and a lack of cohesion throughout a team registering nine changes.
Toulouse, who had won only three matches prior to this game, had been thrashed 5-1 at Anfield a fortnight ago but were an entirely different prospect on home turf, although they benefited from some shambolic defending.
Liverpool still top the group but their advantage has been cut to just two points and although they have the two weakest sides still to play Klopp’s 450th game in charge was not one to remember as they slipped to their first European defeat this season.
The only cause for celebration on the night came a couple of hours before kick-off when news came through from Colombia that Luis Diaz’s father had been released from his 12-day kidnap ordeal.