Dries Mertens and Fernando Llorente struck late to earn Napoli a 2-0 win at home to holder Liverpool in the first game of the Reds' Champions League defence.
Carlo Ancelotti's men won the corresponding fixture last term with Mertens' spot-kick and Llorente's injury-time goal enough to ensure history was repeated in the Group E clash at the Stadio San Paolo on Tuesday.
Andy Robertson was deemed to have tripped Jose Callejon in the box and, after VAR ratified the penalty decision, Mertens squeezed his penalty past Adrian in the 82nd minute.
Liverpool rode its luck in reaching the knockout rounds in 2018-19 and Jurgen Klopp's men will again have to bounce back from an away loss to Napoli this year after Llorente's first goal for the club sealed all three points.
Napoli had an early strike ruled out for offside when Hirving Lozano headed home the rebound after Adrian's excellent double save from Fabian Ruiz.
READ: Liverpool not favourites against 'cheeky b*******' Napoli, says Klopp
Sadio Mane's shot was saved by Alex Meret in the 20th minute - Liverpool recording its first shot on target in the game having failed to manage any in last season's visit.
And the Reds should have gone into the break 1-0 up, Firmino heading wide a fine James Milner cross on the Brazil forward's 200th Liverpool appearance.
Napoli had the first big chance of the second half, Adrian showing superb reactions to prevent Mertens from turning in Fabian's deep cross, then Mane overhit a pass to Mohamed Salah as Liverpool broke at speed.
Liverpool was starting to build pressure and, after successive errors from Kalidou Koulibaly and Kostas Manolas handed him a sight of goal in the 65th minute, Salah's drive was turned around the post by Meret.
Napoli's goalkeeper had to deny Mane again as Liverpool looked to finish strongly, but when Callejon jinked into the box he went over Robertson's outstretched leg to win a penalty.
Mertens had to wait for the VAR check, but calmly drilled his strike past Adrian, with Virgil van Dijk's terrible error in stoppage time ensuring former Tottenham striker Llorente could ease home a second.
What does it mean? History repeated in Naples
Lorenzo Insigne's late strike earned Carlo Ancelotti's side a 1-0 victory against Liverpool last season and lightning struck twice, with Liverpool becoming the first holder to lose the first game of its Champions League defence since AC Milan did so in 1994-95.
Liverpool has kept only one clean sheet in eight competitive games this season, which must worry Klopp, especially as reliable leader Van Dijk was badly at fault for Llorente's clincher.
Mertens the matchwinner
An 11th Champions League goal from Mertens set up this win, with the Belgium international also helping to force Van Dijk's error for Napoli's second goal.
Ancelotti named four attackers in his starting XI with the three-time Champions League winning coach's bold selection justified by an eye-catching win.
Another away blank for Salah
Chances were at a premium for both sides for most of the game, but Salah is a player expected to create opportunities for himself. He failed to do so against a tough defence, although Mane undoubtedly should have set him up.
The Egypt star has now failed to score in all three away appearances for Liverpool this season.
What's next?
Liverpool travels to Chelsea in a blockbuster Premier League clash on Sunday, the same day Napoli goes to Lecce in Serie A. When the Champions League returns for matchweek two early next month, Anfield will welcome early group leader Salzburg with Napoli going away to Genk.
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