Liverpool have lost 3-2 to Fenerbahce despite taking the lead twice in an incredibly frustrating evening for Andoni Iraola’s side.
Treymaurice Nyoni gave Liverpool the advantage, but within four minutes his goal was countered by Mason Greenwood’s deflected free-kick.
Alexander Isak then put the Reds back ahead, but their lead lasted only four minutes again after Archie Brown tapped home from close range.
Substitute Vedat Muriqi dealt the crushing blow to win the game for Fenerbahce as the Turkish side’s manager Dirk Kuyt proved to haunt his former club.
Three minutes in, Victor Munoz had a couple of chances to get a strike on goal but couldn’t get past former Manchester City goalkeeper Ederson at his near post.
The Reds dominated proceedings in the opening 20 minutes, retaining possession well as Fenerbahce were forced to do the hard yards.
Joe Gomez nearly turned provider after a brilliant cross into the six-yard box missed everyone as Liverpool started to grow in confidence.
The home side’s first sniff at a chance came when Greenwood was played in behind but was knocked off balance by Kostas Tsimikas.
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The Greek arguably got lucky not to give away a penalty after his strong challenge sent the English winger down, but VAR cleared Fenerbahce’s claim.
Moments later, Nyoni got on the scoresheet after the ball fell to the youngster on the volley and his deflected shot went past Ederson to give Liverpool the lead.
The goal seemed to fuel the home atmosphere, as Fenerbahce looked for a quick response after a dangerous delivery into the penalty area was met by Irfan Kahveci, whose close-range strike hit the bar.
The Turkish side’s response paid dividends after Greenwood struck a free kick from distance, which took a wicked deflection off Jeremy Jacquet and past Allison to level the score.
The Brazilian was fuming with his centre-back for turning his back on the ball, as the Reds’ lead lasted all of four minutes.
Greenwood nearly got his brace just before half-time, driving down the byline and hitting a left-footed strike that Allison saved well.
Rio Ngumoha nearly caught out Ederson at his near post early in the second half, but the Brazilian got down to parry behind for a corner.
The resulting set-piece reached Virgil van Dijk’s head, but his effort went straight down Ederson’s throat.
Andoni Iraola rolled the dice and made three substitutions with 25 minutes to play, who had an immediate impact on the game.
Cody Gakpo found his way to the byline and lifted a brilliant ball into Isak, whose powerful header beat Ederson and gave Liverpool the lead.
In a carbon copy of the first half, the Reds’ advantage was short-lived after Gakpo inadvertently flicked on a hopeful N’Golo Kante delivery past an on-rushing Allison.
Brown was left alone at the far post to tap home and level the tie with 15 minutes to play.
The Fenerbahce faithful were then sent ballistic after a header from substitute Muriqi beat Allison to put the Turkish side ahead after some woeful Liverpool defending.
Three red shirts crowded around the Kosovan, but he was still able to stand his ground and head past the Brazilian.
Fenerbahce saw out the contest and dealt Liverpool their first Champions League loss of the season.
Speaking after the game, Liverpool defender Tsimikas told Uefa: “Congratulations to Fenerbahce, they deserve it. We didn’t play how we had to play.
“We didn’t defend after the goal we conceded; after three or four minutes, automatically, we conceded another goal.
“I think we have to mark better if we want to win games. We didn’t play very good and that’s why we lost.”
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