Lorenzo Insigne starred as a poor Liverpool performance was punished with a 3-0 defeat to Napoli at Murrayfield.
Insigne took advantage of some poor Liverpool defending to cut in on the break and curl the ball past Simon Mignolet for his opener after 17 minutes, before again exposing Trent Alexander-Arnold's positioning to set-up Arkadiusz Milik who slid in a second 12 minutes later.
A briefly improved Liverpool performance after the break was dealt a blow when Insigne turned Alexander-Arnold one-on-one and Amin Younes tapped in the rebound from Mignolet's initial save seven minutes after the break.
Liverpool: Mignolet, Alexander-Arnold, Matip, Van Dijk, Robertson, Henderson, Fabinho, Milner, Oxlade-Chamberlain, Origi, Wijnaldum.
Jurgen Klopp's side struggled to create chances throughout and only caused Napoli goalkeeper Alex Meret any real difficulty in the final minute, when substitute Harry Wilson forced him into a full-length save.
How Liverpool's poor pre-season continued
Whether this was a case of fitness over performance or not, Liverpool's level of intensity was lacking from the start and after Divock Origi side-footed Andrew Robertson's perfect cross wide inside four minutes, the Reds failed to create another chance of note before half-time.
In the meantime, Napoli were happy to bide their time and enact a smart tactical plan on the break, which came to fruition a quarter of an hour in when a fine pass out to the left flank caught Alexander-Arnold upfield, and with Joel Matip backing off he cut inside and curled the ball beyond Mignolet from 20 yards.
Another rapid break led to the Italian side's second when Liverpool gave the ball away in midfield and Insigne was rapidly found again, reaching a crossing position before picking out Milik with a low ball which he slid in to turn into the far corner.
In first-half injury time Matip rose highest to nod James Milner's cross wide but Liverpool needed something more, only to find themselves three down seven minutes after half-time when Insigne was again found on the left flank, and after turning inside of Alexander-Arnold his shot was parried away by Mignolet, but left Younes with a simple finish.
A flurry of changes in the final 20 minutes improved matters for Liverpool, with Rhian Brewster and Wilson full of running, and 16-year-old Harvey Elliott, only signed from Fulham earlier on Sunday, firing wide after a smart take.
But it still took until the final minute for them to give Meret something to show for his afternoon's work, as Wilson was given time to line up a shot on his left and pulled a diving save out of the goalkeeper from 20 yards.
Should Liverpool be worried?
It's very early to say, but their pre-season form is certainly worse than they would've hoped, with one draw and three defeats from their last four games.
Mohamed Salah, Sadio Mane and Roberto Firmino are still to return to training, but a first-choice defence has looked shaky in those recent matches and was cut apart far too easily against Napoli.
But how much of this, if any, will transfer to competitive games is difficult to say. It would be no great surprise if Liverpool returned to their solid best and saw off Norwich on August 9, live on Sky Sports in their Premier League opener.
Klopp: We need our freshness back
Jurgen Klopp admitted he wasn't happy with Liverpool's run of pre-season form after their third defeat from four, but said he would use this week ahead of the Community Shield to get his players' freshness back in time for the new season.
"We have another week which we will use to get freshness back," he said. "But we have to make better decisions. It was not good, of course.
"We have lost a few games, we try to use them and I am pretty sure we will play better football when necessary."
Liverpool play Lyon in Geneva at 6pm on Wednesday, before the Community Shield next Sunday against Manchester City at Wembley at 3pm