When it comes to comebacks, Liverpool and Istanbul have plenty of history - but this time Andoni Iraola's side made the wrong kind.
Having hit the 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 Iraola's players then capitulated amid a febrile atmosphere, as spirited hosts led by interim boss Dirk Kuyt - a Liverpool hero of years gone by - pulled off a shock comeback victory.
By losing 3-2 at the Sukru Saracoglu stadium, Iraola's visitors created that unwanted slice of history: this was the latest they have ever gone ahead in a major European game and then been beaten.
As Liverpool saw three points slip from their grasp, Kuyt said his players had tapped into the mindset that has allowed the Reds to achieve so many great feats in Europe in the past.
He joined Liverpool in 2006, a year after the team's famous 'Miracle of Istanbul' comeback in the Champions League final.
"We told each other to stick together and be united. That's something I learned from Liverpool, who we played against," Kuyt said. "We made a miracle tonight - not many expected us to win."
Fenerbahce will remember this one for a long time. Liverpool will want to quickly forget it.
After winning five games in a row, Iraola's side have gone on to lose twice in four days. Arsenal on Sunday, and now this.
On the flight back from Istanbul, there will be plenty of disappointment at the way in which Liverpool failed to see this game out.
"It's frustration because it's a difficult place to come and play," said Iraola. "We were, during most part of the game, thinking we can win this one. But obviously it hasn't happened."
All three of Fenerbahce's goals came from set-pieces.
Two were scored by Englishmen.
Former Manchester United forward Mason Greenwood benefited from a slice of luck when his free-kick deflected in off Jeremy Jacquet in the first half for Fenerbahce's first equaliser, and Liverpool only had themselves to blame when Cody Gakpo's header took the ball past Alisson and gave Birmingham-born Archie Brown a tap in to make it 2-2.
Six minutes later, Liverpool made a mess of Brown's looping ball in the box and Vedat Muriqi beat three players in red and headed the ball past Alisson.
"They are cheap goals. They are messy goals," said Iraola.
"It's a free-kick. It's quite far also and it's through the wall.
"Mistakes can cost you. For the last goal, it's a long throw and the first phase is controlled but after a very long ball, Muriqi wins it.
"The second goal, Cody is the one touching the ball just in front of Ali [Alisson].
"In the stadium it was almost impossible to communicate because it was so noisy. It was even difficult for me to give any kind of instruction. I suppose the communication between Ali and Cody was difficult."
After showing signs of genuine progress in recent weeks, Liverpool let potential victory slip away here 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 ex-Liverpool defender Stephen Warnock, who was watching the game for Match of the Day.
"It was a much-changed team. However, the simple mistakes that they made from set-pieces or simple balls into the box are not good enough.
"The frustrating part for Liverpool fans is that we all know what the problems are. So, where is the solution? That's what Iraola is trying to do at the moment, but it's just a question of how long it takes.
"The biggest issue is that this keeps on happening, with Liverpool looking like they can concede at any moment and being so open on the counter-attack. There is a repetitive theme of the goals they are conceding and it undoes all the good work they do when they go forward.
"When you go ahead, twice, away from home at Fenerbahce in the Champions League then, if that is Arsenal they win that game - they see it out against a team like Fenerbahce.
"Liverpool don't have the ability to do that at the moment, and that is what is really frustrating."
