Arne Slot has achieved a rare, unwanted record after Liverpool were beaten 1-0 by Galatasaray in the Champions League round of 16 fist leg on Tuesday night.
Liverpool suffered defeat in Istanbul at the hands of the Turkish champions for the second time this season, with former Southampton, Fulham and Wolves midfielder Mario Lemina scoring the only goal of the game in the seventh minute.
The Reds did have the ball in the net from a Dominik Szoboszlai corner in the second half but it was ruled out after a VAR review found that the ball had struck Ibrahima Konate's arm twice beforehand.
Liverpool suffered the same result at Rams Park as they did in the league phase back in September and must overturn the deficit in the second leg at Anfield on 18 March.
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It was Slot's side's third defeat of the season in the Champions League and a 14th overall in all competitions.
But the latest loss came at a significant milestone for Slot, who has endured a difficult second season after guiding the Reds to a 20th league title in his first campaign.
It was Slot's 100th game as manager of Liverpool and according to talkSPORT, he became the first Reds manager to lose on the century of matches since the legendary Graeme Souness back in 1992.
Remarkably, if Liverpool had beaten Galatasaray, Slot would have been celebrating the best ever record for a manager in his first 100 games at the Merseyside giants.
Slot picked up 62 games in his first 100 matches, the exact same record as club icon Kenny Dalglish in his first stint at Anfield.
Jurgen Klopp, the man who Slot replaced, won half of his first 100 games - whereas Rafa Benitez picked up 54 wins in his first century.
Prior to the defeat in Turkey, Slot expressed pride at reaching 100 games in charge of Liverpool and paid tribute to his players.
“It makes me really proud that I’ve become the Liverpool manager and that it’s going to be my 100th game," Slot said in his pre-match press conference.
“I don’t think it’s a bad track record in those hundred games, although sometimes you get a different feeling about that.
“It’s nice that my 100th game is such a nice game to play, a last 16 Champions League game against Galatasaray.
"But it’s never about the manager, it’s about the players. I try to prepare them just like all the other 99 games I've done before.
“But then it’s always the players who have to go out and perform, and I’ve been very lucky that I’ve been given such a good team in both seasons."
Slot having the opportunity to get to 150 or 120 games may hinge on Liverpool's performance in the Premier League.
Liverpool are currently sixth in the league, three points behind Aston Villa in fourth. They return to action on Sunday with a visit of Spurs, who were thrashed 5-2 by Atletico Madrid in a second defeat for England's sides on Tuesday.
Josh Lawless