Liverpool twice led but found a way to lose at Fenerbahce as their perfect record in the Champions League came to an end on a rain-soaked night in Istanbul.
Vedat Muriqi had the decisive moment in a five-goal thriller that saw Liverpool's defensive flaws exposed as they failed to control a game they had within their grasp.
A Night of Deflected Goals and Missed Leads
Trey Nyoni's deflected volley had the Reds in front as they looked to respond following their loss to Arsenal on Sunday, but their lead didn't last long as Mason Greenwood's effort, which was also deflected, levelled the game.
Alexander Isak came off the bench with half an hour remaining and needed just minutes to put the Premier League side in front, but Andoni Iraola's side again failed to keep hold of their advantage as Nathan Brown got Fenerbahce back on level terms.
Muriqi, who replaced Romelu Lukaku, later headed home from a looped cross as questions were asked of Alisson's failure to come and claim.
Greenwood Threat and Nyoni's Opener
Greenwood was Fenerbahce's biggest threat and the ex-Manchester United forward was sent clear but went down under pressure from Kostas Tsimikas, but the penalty appeals from the home side were waved away.
That frustration was compounded only minutes later as Liverpool teenager Trey Nyoni opened the scoring. His volley from the edge of the box went in via a deflection, leaving Ederson with no chance as the jeers rained down from the home fans.
The Turkish side hit the bar moments later as Ismail Yuksek's effort hit the woodwork, denying the hosts an immediate equaliser, but they weren't to be denied as Greenwood did level the contest. Liverpool led for just four minutes with the forward's free-kick flying in off Jeremy Jacquet.
Fenerbahce's Comebacks and Kuyt's Role
The Reds had won just four of their 11 visits to Istanbul, but were coming up against Fenerbahce for the first time. Dirk Kuyt, a man who scored 71 times for the Reds and played in the 2007 Champions League final for them, is currently in charge of the Turkish outfit.
Virgil van Dijk's header was Liverpool's first major chance of the second half, and had his effort been either side of Ederson then he may well have been in trouble. Isak though was on hand to convert when he had his chance from close range, nodding Liverpool in front for the second time on the night.
Much like the first half though, the Reds' lead was short lived. Brown, who came through the ranks at Derby, scored four minutes later at the back post to restore parity. And things would get even better for Kuyt and Fenerbahce, who saw Muriqi head home the winner with 11 minutes left.
Familiar Flaws and Barcola's Struggles
Liverpool had a night where they simply didn't want to hold onto a lead, and they ultimately left Turkey with nothing as their game management is seriously called into question.
The team who were beaten 6-0 at Aston Villa less than a month ago showcased their powers of recovery on numerous occasions across the evening, but for all their good work Liverpool will wonder how they twice led but ultimately ended up losing.
Iraola's side were only in front for a total of eight minutes despite twice putting themselves in front as Fenerbahce continued to hit back at speed. This was the fourth time they've conceded three goals in their last seven games.
Irrespective of the result, it was soon apparent that having Barcola as the central point of Liverpool's attack was not going to be a long-term thing. The Frenchman was given the nod in one of the more surprising selection calls of the night. Him playing wasn't a surprise. Him playing as the No 9 with Alexander Isak on the bench was.
Barcola's USP has long been his pace, and that is best used out on the flanks. Naturally the ex-PSG man is not the most physical, nor is he renowned for his ability to bring others into play. There's no doubt it stunted Liverpool's attack, which relied heavily upon the individual quality of Rio Ngumoha.
In a Liverpool midfield that has Dominik Szoboszlai, Alexis Mac Allister and Ryan Gravenberch, Nyoni continues to enjoy the backing of his manager and he's more than repaying that faith. The 19-year-old scored the first goal of his career in Istanbul as he made the most of the space he was afforded on the edge of the Fenerbahce box.
Despite his age Nyoni never looked overawed, and the most pressing problem for Iraola could be explaining to one of his most established stars why a teenage star has leapfrogged them in the pecking order. There's no doubt he outshone Szoboszlai in the middle of the pitch, with the Hungarian's displays increasingly coming under scrutiny.