Everton secured their first win in a Merseyside derby at Goodison Park since 2010 to leave Liverpool's Premier League title aspirations in ruins after a 2-0 defeat on Wednesday.
Defeat leaves Jurgen Klopp's men still three points adrift of leaders Arsenal and only one point in front of defending champions Manchester City, who have two games in hand.
"We need a crisis at City and Arsenal and we need to win football games," said Klopp of his side's shot at the title with four games to go of his reign.
Goals from Jarrad Branthwaite and Dominic Calvert-Lewin took Everton eight points clear of the relegation zone.
The Toffees now look certain to extend their 70-year stay in the English top flight despite being deducted eight points on two charges of breaching financial rules.
Klopp had never lost on his previous eight visits to Goodison but his final taste of the Merseyside derby was a bitter one.
Hopes of a glorious goodbye for the German after a nearly nine-year tenure that has transformed the club's fortunes are fading fast.
"If we play like today we have no chance to consider ourselves in the race," said Liverpool captain Virgil van Dijk.
"I think everyone has to look in the mirror and look at their performance and if they’ve given everything. Do they really want to win the league?"
According to reports, Feyenoord boss Arne Slot is being lined up as Klopp's successor and the past few weeks have exposed weaknesses that need addressing in a huge summer for the Liverpool hierarchy.
- 'Energy, commitment' -
The Reds have won just one of their last four league games and have also bowed out of the FA Cup and Europa League in recent weeks.
Klopp made six changes after resting a number of key players for Sunday's 3-1 win at Fulham but did not get the response he desired.
Buoyed by their weekend win over Nottingham Forest to pull clear of the relegation zone, Everton are a side transformed from the one that went 13 Premier League games without a win between December and April.
"Delighted with the performance of our players and delighted for the Evertonians," said Everton boss Sean Dyche.
"They're a good side, we know that. The commitment and energy from us had to be there."
Slow starts have been a recurring factor as Liverpool's quest for four trophies has unravelled.
Everton thought they had a penalty in the opening minutes when Calvert-Lewin was tripped by Alisson Becker but VAR intervened to save the visitors as the striker was offside.
Alisson then clawed away a Calvert-Lewin header and Ben Godfrey nodded wide as Liverpool struggled to cope with Everton's threat from set-pieces.
More comical defending from the Reds led to the opener on 27 minutes.
Alexis Mac Allister's mishit fell perfectly for Branthwaite and the defender's effort went in off the post despite Alisson's best efforts.
Going behind woke Liverpool from their slumber and only a combination of wasteful finishing and Jordan Pickford preserved Everton's lead until half-time.
Darwin Nunez blasted straight at the England number one when clean through before the Uruguayan teed up Luis Diaz to fire too close to Pickford.
Mohamed Salah's loss of form has come at the worst possible time for Liverpool's title challenge and the Egyptian sliced another good opening well over the bar.
Liverpool were camped in the Everton half after the break, yet the hosts pulled further clear just before the hour mark from another dead ball.
Calvert-Lewin was afforded a free header at the back post to power home Dwight McNeil's corner.
Liverpool's night was summed up when Diaz's powerful effort came back off the post with Pickford finally beaten.
But it was Klopp who was crestfallen come the final whistle as he looks set to depart Anfield with just one Premier League title to his name.
Klopp's farewell fizzles out tamely
Jurgen Klopp's nearly nine years at Liverpool have been filled with memorable milestones but an unwanted first of his reign leaves his final few weeks at Anfield with little left to play for.
Klopp tasted defeat in the Merseyside derby at Goodison Park for the first time in nine visits as a 2-0 defeat against Everton left the Reds' dreams of sending their manager off as a Premier League winner in tatters.
Just a few weeks ago, Liverpool were on course for a potential quadruple but have come off the rails.
A run of four wins in nine games has seen Klopp's men crash out of the Europa League and FA Cup as well as falling off the pace at the top of the Premier League.
Liverpool trail leaders Arsenal by three points and are only one point ahead of defending champions Manchester City, who have two games in hand.
AFP Sport looks at what has gone wrong to leave Klopp's fitting farewell at risk of fizzling out.
Slow starts
Liverpool's habit of fighting back from losing positions was lauded earlier in the campaign as a sign of the "mentality monsters" Klopp has created throughout his time at Anfield.
They have amassed 27 points after falling behind in the Premier League alone this season, but have seen their luck run out after falling behind to Crystal Palace and Everton in shock defeats over the past 10 days.
In all competitions, Liverpool have conceded the opening goal 22 times this season.
They never recovered from a sluggish start at Goodison as Everton wasted a number of chances and had a penalty overturned by VAR even before Jarrad Branthwaite opened the scoring on 27 minutes.
Wasteful finishing
Liverpool's forward line has also gone off the boil come the business end of the season.
They have failed to score from open play in four their last five games.
Mohamed Salah has looked out of sorts since returning from a hamstring injury picked up at the Africa Cup of Nations.
Luis Diaz and Darwin Nunez were again guilty of wasting huge chances against Everton.
And Diogo Jota, often heralded as the most natural finisher at the club, has been sidelined again by injury after just returning from a two-month layoff.
"You can see we are in a rush in front of goal," said Klopp. "We create a lot but we don't score often enough.
"You can see that and that's the problem. You have to fight through these periods. It's not a problem of attitude, the boys want it but it is my job to bring them into a situation where they feel confident to do it."
Fatigue
The quest for the quadruple could now be coming back to haunt Klopp as Liverpool look to have run out of steam.
They have played 54 games this season and will have four more before the end of the campaign.
A number of academy graduates stepped up during an injury crisis in the early months of 2024 and helped ensure Klopp did at least secure some silverware in his final season by winning the League Cup in February.
Yet, just as they are getting major players back with Alisson Becker and Trent Alexander-Arnold returning in recent weeks, those that have been relied on most during the winter months are fading.
Klopp admitted after the Palace match that midfield duo Alexis Mac Allister and Wataru Endo are struggling due to the burden placed upon them earlier in the campaign.
"Players who played all the games are less fresh but it is the same for the other teams. I don't want that to be an excuse," added Klopp.
"A lot of things come together so it is not great timing. I would prefer to be sitting here winning 4-0 and flying but the job is to win football games and the more you win, the more successful you are.
"In the moment we didn’t win enough to get anything from the season."