A late collapse saw Liverpool begin the defence of their Champions League crown with a 2-0 defeat to Napoli.
A Dries Mertens penalty put the hosts ahead at the San Paolo with 10 minutes remaining, before substitute Fernando Llorente sealed the win for the Italians in stoppage time.
The game’s defining moment arrived on 82 minutes, when referee Felix Brych pointed to the spot after Jose Callejon went down under the challenge of Andrew Robertson.
There appeared to be minimal contact but, after a VAR review, the decision was upheld.
A calamitous finale for Liverpool was compounded when a rare Virgil van Dijk error saw the Dutchman play a loose backpass to Llorente, who doubled Napoli’s lead.
Liverpool struggled to create clear-cut chances throughout the match, with both Sadio Mane and Roberto Firmino guilty of passing up presentable opportunities.
It means Jurgen Klopp’s team have lost their last four away games in the group stage of this competition, including a 1-0 loss to Napoli in last season’s competition.
Napoli did find the back of the net after just seven minutes. Lorenzo Insigne rolled the ball back for Fabio Ruiz, who forced a save from Adrian with a fierce drive before working the Spaniard with an almost identical effort from the rebound.
Hirving Lozano headed home after a second Adrian save but the flag was raised for offside.
An energetic opening, however, did not continue and Liverpool’s first shot on target didn’t arrive until the 20th minute. Jordan Henderson capitalised on sloppy play in midfield and chipped a pass through for Mane to fire a bouncing effort at Napoli goalkeeper Alex Meret.
It was a first half low on quality. Napoli carried greater menace while creating no meaningful chances as Liverpool looked to raid on the counter attack. Mohamed Salah scuffed a speculative effort wide on 36 minutes, summing up the visitors offensive performance to that point.
Seconds later, a promising Liverpool break stalled when Firmino lingered in possession on the edge of the Napoli penalty area.
A cohesive Liverpool attack did follow soon after as Firmino neatly controlled Henderson’s punt up field. He slipped a pass through to James Milner but the midfielder’s low cross towards Salah lacked precision and was easily cut out.
From the resulting corner, Firmino wasted Liverpool’s first clear-cut chance of the contest. Milner’s cross was far better on this occasion and it found the Brazilian all alone, only for Firmino to head wide from 12 yards out.
Early in the second half, Adrian pulled off a stunning save to deny Mertens. The Belgian’s cushioned close-range volley from Rui’s cross was heading high into the net before the stand-in goalkeeper hurled himself into action and flicked the ball over the bar with his flailing right hand.
Mane spurned a glorious opportunity for Liverpool in the 54th minute. A Napoli corner was well cleared and the Senegalese forward led a charge upfield. With just one defender back for Napoli and Salah alongside him in attack, Mane waited too long to play in his Egyptian teammate and, when his pass eventually arrived, it was over hit.
A horribly mishit clearance by Kostas Manolas inadvertently let Salah in with 25 minutes to go. Meret got down well turn his low drive around the post.
Liverpool grew in stature and began to take charge of proceedings as the game headed into the final quarter.
But, just as Klopp’s men were enjoying the upper hand, Napoli were awarded a penalty as the contest entered the final 10 minutes.
Callejon skipped inside of Roberston and promptly went to ground. The referee pointed to the spot and, despite a VAR review, his initial decision stood.
Mertens finally got the better of Adrian, who did get a hand to the well-struck penalty but was unable to keep it out.
Llorente sealed the win for Carlo Ancelotti’s team, Van Dijk’s mistake summing up an awful closing period.
Next up for Liverpool is a home match with Salzburg, who began their campaign with a 6-2 thrashing of Genk.
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