Defeat to Leeds United on Saturday marked the latest low point of Liverpool's season, with the Reds now 15 points adrift of Premier League leaders Arsenal.
A glimmer of hope for Jurgen Klopp is that his side are safely through to the knockout stages of the Champions League before their final group game against Napoli. Tuesday's clash with the Serie A side conjures up memories of a group game between the two sides back in December 2018, although Klopp may also be concerned when he looks back on that game.
Heading into the final match of that year's group stages, they had to beat the Italians to go through to the knockout stages. They sat third in Group C ahead of the visit of the Partenopei, with Klopp calling on his players to bounce back from their poor run in the competition to that point.
“We are in a good moment for weeks and months as a club and a team, we have to use it. One of the most difficult teams to play at this moment is Napoli. They are a really good side but we are as well," he said.
“The competition is like this. You play the strongest teams and if you want to go through you have to win. We didn’t win often enough to be through already. That is our mistake and now we can put it right if we perform."
Unsurprisingly for such a crunch clash, Klopp called upon a familiar line-up to get the job done. Alisson started in goal, having arrived that summer from Roma, with Trent Alexander-Arnold, Virgil van Dijk, Joel Matip and Andy Robertson ahead of him in defence.
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The since-departed Georginio Wijnaldum lined up in midfield alongside Jordan Henderson and James Milner. And Napoli also faced the deadly frontline trio of Mohamed Salah, Roberto Firmino and Sadio Mane.
Salah and Alisson played a critical role in a 1-0 win for the Reds, with the former opening the scoring 34 minutes in. He escaped the attention of Kalidou Koulibaly, before firing past David Ospina to net a crucial goal.
Liverpool needed to win with a clean sheet to overtake Napoli in the standings, with Alisson delivering a stunning performance to secure it. The highlight of his display was an incredible save in injury time to prevent Arkadiusz Milik from equalising, leaving Klopp in awe of his keeper.
"If I knew Alisson was this good I would have paid double. The goal Mo scored - what a goal, unbelievable - but the save Ali [Alisson] made I have no words for that. That was the lifesaver tonight," he said.
"It was wild and there were lots of counter attacks but we were ready for that. That is Anfield live and in colour. Wow, what a game. I am not sure a manager could be prouder of a team than I am."
Following the win, former Liverpool star Mark Lawrenson singled out the squad depth that Klopp could call on as they key factor. Lawrenson believed that the strength of the players the Reds had at their disposal made them an intimidating proposition.
"There are many different ways to judge Liverpool's development under Jurgen Klopp but I see their squad strength as the best way to gauge their progress, and it will also play a big part in any future success," he told BBC Sport at the time.
"Look at the players who did not start their win over Napoli on Tuesday night and you can see the Reds now have true depth as well as a quality first XI.
"That is significant because Klopp's style of football is extremely taxing, but it becomes particularly important now they are contenders in the two biggest competitions going into the second half of the season.
"Their squad has already played a key part in that dual challenge, and it is the biggest reason I think they could go the distance on both fronts.
"They will give it a really good go and, with the squad that Klopp has built, they are well equipped this time to build on the position they have put themselves in."
Lawrenson's analysis from four years ago underlines a worry about the current squad that Klopp can call upon though. Nine members of the starting line-up, as two of the three substitutions Klopp made remain at the club.
That suggests that the team has not been refreshed from that day, which is now causing the German painful problems. Liverpool now appear to be an aging team, with too many players not performing to their previous level.
Darwin Nunez was the sole major signing of the summer, but he has endured some growing pains as he adjusts to the Premier League. Klopp may need to look back on Lawrenson's praise as the route out of his side's current struggles.
While a refresh of the team will have to wait until at least the January transfer window, Klopp can begin to put plans in place to bring in new faces. It may also do them well to move on the likes of Milner, who are clearly approaching the end of their career at the top level.
The result on Tuesday will not matter too much to Liverpool, with Napoli secure in top spot in Group A thanks to a vastly superior goal difference. But the clash may well represent the opposite side of the climb that the Reds were making when they faced the Italians four years ago.
