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.
We look 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."