The old fox, as Carlo Ancelotti was once described by Jürgen Klopp, has pestered Liverpool once again. His Napoli team arrived at Anfield in the midst of a footballing civil war but fought tirelessly to deny the European champions safe passage to the knockout stage of the Champions League. There can be no stroll in Salzburg for Liverpool as a consequence.

Europe holds few surprises any more for Klopp, who was taking charge of his 100th game in Uefa competition, and his latest encounter with Napoli brought all-too familiar problems for Liverpool. They were punished by the clinical Dries Mertens and kept comfortably at bay when their performance and their pressure belatedly improved. Dejan Lovren’s second-half equaliser left Anfield anticipating another stirring comeback but it was not to be.

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The opportunity to seal first place and qualification from the group was missed on a relatively flat European night at Anfield and Liverpool must avoid defeat in Salzburg next month to maintain designs on a third consecutive Champions League final appearance. A potential ankle ligament injury to the influential Fabinho increased Klopp’s problems.

The Liverpool manager prediction of a peak Napoli proved correct. The visitors have been in turmoil thanks to a confrontation with the club president, Aurelio De Laurentiis, who has fined players and imposed a media blackout over their refusal to attend a training camp that he demanded following their Champions League draw with Salzburg. But they started vibrantly and dangerously at Anfield, their run of six games without a win forgotten at kick-off, and stuck rigidly to Ancelotti’s plan to deny Liverpool space in central midfield and force the hosts out wide.

The quality of Trent Alexander-Arnold’s deliveries was sorely missed as the right-back was rested among the substitutes until the final stages.

Facebook Twitter Pinterest Dries Mertens scores the opener for Napoli. Photograph: Robbie Jay Barratt - AMA/Getty Images

Liverpool suffered their first blow when Fabinho was forced off injured after 19 minutes. The Brazilian stayed down after an innocuous looking challenge in central midfield and, despite attempts to continue, had to be replaced by Georginio Wijnaldum. He departed Anfield wearing a protective boot and facing a potentially lengthy absence.

Their midfield was still adjusting when Napoli inflicted the second blow. The opening goal was superbly taken by Mertens, who timed his run to perfection to latch on to Giovanni Di Lorenzo’s ball over the top, took time to measure his angle with Lovren flailing in pursuit, and found the far corner of Alisson’s goal with a precision finish. But there was also an element of controversy.

Virgil van Dijk felt Mertens should have been penalised for a foul when the pair came together for a clearance by Napoli goalkeeper Alex Meret. The forward was certainly looking at his man and not the ball when he caught the defender’s hip but, following a lengthy VAR review, the goal stood. There then followed a second VAR check for offside. Three minutes were wasted in total. The goal stood and Liverpool’s blood began to boil at the referee Carlos del Cerro Grande.

Klopp stared in disbelief at the Spanish official over his refusal to award the free-kick that Van Dijk wanted. He grew increasingly agitated over a series of calls in Napoli’s favour and lost it completely when Del Cerro Grande dismissed Sadio Mané’s appeal for a penalty as Liverpool rallied late in the first half. Di Lorenzo touched Mané’s shoulder as the striker weaved his way inside the area before going to ground – too easily for the referee’s liking who waved play on. A foul on Mané by Allan prompted another outburst from the Liverpool manager and he received the first yellow card of the contest.

Liverpool created little before the interval and were uncharacteristically careless in possession. Kalidou Koulibaly and Kostas Manolas, the visiting central defenders, were often perfectly placed to deal with all manner of deliveries into their area. When James Milner did break the blue line, weaving his way past three players with impressive flair, Meret held his position well to save at the near post.

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The home side’s accuracy on the ball, intensity and movement improved considerably in the second half, however, and despite a few uncomfortable moments for Joe Gomez the game was otherwise confined to deep inside the Napoli half. A mistake by Meret presented Liverpool with their first clear opportunity when, attempting to collect Jordan Henderson’s out-swinging cross, he dropped the ball at the feet of Roberto Firmino. The Brazilian hooked goalwards but Koulibaly was alert to the danger and cleared off the line with a knee.

Mohamed Salah shot straight at the Napoli keeper when found in space by Andy Robertson. His reaction told that he should have done better. Firmino sent a stooping header wide from substitute Alex Oxlade-Chamberlain’s cross. The pressure was building and the visitors finally broke when Lovren met Milner’s corner with a towering header that flew beyond the stranded Meret. Napoli appealed for a VAR intervention for an alleged push by Lovren on Mertens. It was as tame as Di Lorenzo’s on Mané earlier and rightly ignored, but thereafter Napoli held firm. All to play for in Austria.