Liverpool suffered their first defeat in the UEFA Champions League this season after losing 3-2 at Fenerbahce on Wednesday evening.
The Reds were in control for most of the game, but were let down by defensive lapses, allowing Fenerbahce to record their first win in the competition since 2008.
Trey Nyoni put Liverpool ahead with a deflected shot in the 25th minute, becoming the youngest player to score his first goal for the club in a European match.
Fenerbahce responded immediately, with Mason Greenwood drawing the hosts level with a deflected free-kick.
The Turkish side then began to control proceedings. Greenwood almost gave them the lead before halftime, but he was denied by Alisson Becker.
Liverpool regained control after the interval and nearly found the net after the hour mark, but Milan Skriniar produced a brilliant goal-line clearance to keep the scores level.
Alexander Isak put them back ahead in the 69th minute, heading fellow substitute Cody Gakpo’s cross beyond Ederson’s reach.
Just as they did in the first half, Fenerbahce responded well to falling behind and took advantage of Liverpool’s poor defending to turn the game around.
Archie Brown restored parity for the hosts, running in behind Dominic Szoboszlai to tap the ball into the net.
Moments later, Brown delivered a brilliant cross into the area for Vedat Muriqi to complete the turnaround and score his first-ever Champions League goal.
Liverpool had never previously taken the lead so late in a major European match and gone on to lose, with Isak’s 69th-minute goal setting an unwanted record.
The Merseyside giants are still in a good position to secure automatic qualification to the knockout stages, having already gathered nine points.
They will now turn their attention to Sunday’s Premier League clash against Crystal Palace.