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When it comes to comebacks, Liverpool and Istanbul have plenty of history - but this time Andoni Iraola's side made the wrong kind.
Having edged in front for a second time against Fenerbahce, when Alexander Isak nodded in after 69 minutes, Liverpool were seemingly on their way to a thoroughly impressive away win.
But the players capitulated amid a febrile atmosphere and Iraola's side created an unwanted slice of history - this was the latest Liverpool had ever gone ahead in a major European game and then been beaten.
Liverpool will want to quickly forget it.
"It is frustration because it is a difficult place to come and play," said Iraola. "We were, for the most part of the game, thinking we can win - but obviously that hasn't happened."
All three of Fenerbahce's goals came from set-pieces.
"They are cheap and messy goals," added Iraola. "It was almost impossible to communicate in the stadium because it was so noisy. It was even difficult for me to give any kind of instruction."
After showing signs of genuine progress in recent weeks, the Reds let potential victory slip away in a concerning manner.
"It feels like a step back from what we saw against Arsenal because everyone thought: 'OK, we are seeing huge improvements from Liverpool,'" said former Reds defender Stephen Warnock on Match of the Day.
"The simple mistakes they made from set-pieces and balls into the box are not good enough.
"The frustrating part for fans is that we all know what the problems are, so where is the solution? That's what Iraola is trying to find at the moment, but it's a question of how long that takes.
"Liverpool look like they can concede at any moment due to being so open on the counter-attack. There is a repetitive theme of the goals they are conceding and it undoes all of the good work they do when they go forward.
"It is really frustrating."