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Liverpool lost its 100 per cent record in the Champions League under Andoni Iraola, with Fenerbahce inflicting yet another difficult defeat to the Reds in Turkiye.
It was a match that highlighted the defensive frailties of the Merseyside outfit, just days on from the attacking unit being questioned in a narrow defeat to Arsenal in the Premier League.
The tie had started in ideal fashion when Trey Nyoni's strike from the edge of the box hit the back of the net, but that lead only lasted four minutes, as Jeremy Jacquet's poor positioning in the wall from a free-kick saw a deflected effort from Mason Greenwood beat Alisson between the posts.
The second half continued in much the same pattern, as Alexander Isak made an instant impact with a header from his first touch of the ball that gave the Reds the lead again. However, just moments later, a mix-up between Cody Gakpo and Alisson meant that Archie Brown had a simple tap-in to level it up again.
Then came the completed turnaround, as just moments later, Brown lofted a ball in the air that none of the Liverpool players got close to. Instead, substitute Vedat Muriqi powered his header goalwards, and secured a famous victory for Fenerbahce on the night.
Plenty of players were at fault for the defensive side of the game, but it was Alisson who was criticized particularly for his role in the goals. Reflecting on the second for Fenerbahce, Ally McCoist said on TNT Sports: "It is a lack of communication between Alisson and Gakpo. It leaves Brown with a simple task at the back post.
"Alisson gets caught in no man's land. Szoboszlai completely switches off as well and Brown sneaks in. He has to be aware of the players around him. Poor header from Gakpo and it's a tap in."
The Brazilian shot-stopper was ripped apart for his role in the eventual winner, with the goalkeeper criticized for his inability to deal with a lofted ball in the box, instead leaving it to his defenders, who were unable to stop the header from Muriqi.
"The ball is in the air a long time - the goalkeeper has to come for that!" McCoist added after the goal. "It is up there a long time. Jacquet doesn't cover himself in glory but it is a brilliant header."
It wasn't just the Scotsman who was left baffled by the decision-making from the veteran goalkeeper, as former Liverpool defender Stephen Warnock echoed his thoughts when speaking on BBC Radio 5Live.
"That was the softest goal yet," the ex-defender said while slamming the display. "There is no physical challenge by a Liverpool player when the ball came in - they were far too weak - and why is Alisson not coming out to claim it?"
It's a defeat that is bruising for the team and the manager, after a relatively positive start in the competition. The Liverpool boss will be hoping it can be a learning point for his group, with the league phase still in a good position for a top-eight finish as things stand.
With a match against Crystal Palace at the weekend before the international break, it's yet another game that Iraola will have to reflect on, with work that needs to be done.