Jurgen Klopp has enjoyed far more victories than defeats during his time at Liverpool, but the Anfield chief is adamant that last week's sorry surrender against Napoli is the worst he has seen his side play.
The Reds travelled to Naples in their Champions League opener against Luciano Spalletti's side with high hopes - but they were systematically dismantled by their Italian hosts. Liverpool found themselves 3-0 down at the break, but it could, and should, have been even more damning with Napoli missing a penalty and striking the post.
The Serie A outfit went on to win the match 4-1 to leave Liverpool with work to do in Group A. Speaking ahead of Tuesday night's crunch clash with Ajax, Klopp admitted: "We had a meeting with the players, I watched the [Napoli] game and it was a real horror, to be honest. It was the worst game we played since I am here."
In the wake of Klopp's admission, Mirror Football takes a look at five of the worst defeats from Klopp's impressive reign...
4-1 Tottenham (2017)
Liverpool's chastening 4-1 defeat against Mauricio Pochettino's side at Wembley was one of the biggest defeats of Klopp's Anfield tenure.
Tottenham ran riot against a fragile Liverpool rearguard - so much so that Dejan Lovren was hauled off after just half an hour by Klopp, who had seen his side ship two goals inside eight first-half minutes.
Simon Mignolet was also scrutinised for his performance, with the Belgian shot-stopper at fault for both of Harry Kane's goals. Unsurprisingly, both Lovren and Mignolet were upgraded by Klopp not long after.
2-0 Red Star (2018)
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Although Liverpool's crushing defeat against Napoli is still fresh in the memory, their calamitous collapse away at Red Star Belgrade has to rank as one of the Reds' worst European nights.
A quick flurry from Milan Pavkov downed Klopp's men, who failed to "find their mojo" during a difficult first half in Serbia.
The Reds rallied after the break, but they were unable to fire back against their opponents, who recorded a famous victory at Liverpool's expense.
7-2 Aston Villa (2020)
Liverpool's Premier League title win, one of the most iconic moments in their recent history, came behind closed doors as they ended a 30-year title drought in the middle of the Covid pandemic.
Unfortunately, one of their worst moments in recent memory followed behind closed doors just months after when they were thumped by Aston Villa at Villa Park.
Ollie Watkins bagged a hat-trick and Jack Grealish ran riot, racking up two goals and three assists in a 7-2 win. Suffering such a heavy defeat so early in the season set the tone for the rest of the campaign for Liverpool, who only managed to clinch a top-four finish on the final day of the season.
3-2 Atletico (2020)
Liverpool claimed their sixth European crown in 2019 - but their bid to defend the Champions League came to an abrupt halt at the hands of Atletico Madrid months later.
The Reds needed to overturn a 1-0 deficit against the LaLiga outfit in the second leg of their last 16 tie at Anfield.
However, a late collapse in extra-time saw Atletico turn the tie on its head, with a last-gasp strike from former Chelsea striker Alvaro Morata enough to eliminate the reigning European champions.
2-0 Everton (2021)
Everton have had a wretched record at Anfield in recent years - but they ended an agonising 22-year wait for a win in their neighbour's backyard in style back in February 2021.
The Toffees took full advantage of a rare slump in form to inflict more misery on Klopp's men, who lost four consecutive league matches for the first time since 1923.
Richarlison and Gylfi Sigurdsson netted in either half to subject Klopp and Liverpool to a rare derby defeat.
