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Liverpool's torrid run continued as they suffered a miserable home defeat by PSV in the Champions League.
The ragged Reds, on their worst run since 1953, have now lost nine of their last 12 matches across all competitions as they were destroyed by the Dutch side at Anfield.
Arne Slot's domestic troubles are well-documented, coming into this match off back-to-back defeats by a three-goal margin, but the Champions League has provided some respite for the Dutch manager and his struggling side.
Three wins in four matches, including a brilliant victory over Real Madrid last time out, had put Liverpool in a strong position in the league phase.
But defeat here left Slot facing serious questions about the current state of this team and just how he is going to fix it.
The visitors went ahead after just six minutes, Virgil van Dijk needlessly sticking his arm in the air in an attempt to claim a foul, but instead giving away a penalty for handball, which Ivan Perisic calmly slotted home.
Dominic Szoboszlai restored parity 10 minutes later when Cody Gakpo's effort was parried away by goalkeeper Matej Kovár, but landed straight at the feet of the Hungarian midfielder for a simple tap-in.
In desperate need of an upturn in results, Liverpool improved as Gakpo went close, while van Dijk's header crashed against the bar.
But the Dutch league leaders restored their advantage when Mauro Junior played a defence-splitting pass and Milos Kerkez could not prevent Guus Til slotting home.
The home side's misery was then compounded as substitute Couhaib Driouech poked in the rebound from Ricardo Pepi's effort, sending the already-buoyant visiting supporters into raptures.
The Moroccan forward then added a second in stoppage time, slotting low into the bottom corner following a swift move, sealing their first victory over an English side since beating Tottenham in the 2008 Europa League and moved up to 15th in the standings.
Liverpool dropped to 13th and will need to improve quickly, but the pressure is on in a fierce battle for a top-eight place.
Liverpool analysis: Where do humiliated Reds go from here?
Liverpool's victory over Real came after victory over Aston Villa in the league and snapped a streak of six defeats in seven matches.
But, what had looked like a revival, quickly took a downturn with back-to-back league defeats leading to more unanswered questions and even whispers of concern over Slot's future on Merseyside.
Another chastening defeat will do nothing to silence those naysayers.
After Szoboszlai's equaliser, Liverpool looked brighter. They played with more urgency and created more chances, Gakpo going close with a powerful header before teeing up Mohamed Salah with a fast pass across the box, but the Egyptian was pipped to the ball.
PSV's second goal stunned Anfield and, from there, the hosts struggled to find solutions.
It was another difficult night for Salah, evidenced when he picked up the ball on the right - just outside the area in prime shooting range - but instead blasted over the bar.
Alexander Isak also again failed to impress when he replaced Hugo Ekitike, who worryingly limped off after an hour, and the Swedish striker's stint on Merseyside continues to disappoint.
Defensively, it was a struggle at times and, as PSV continued to find openings, Liverpool just capitulated.
Left-back Kerkez was the wrong side of his man for the second goal, while Ibrahima Konate missed the ball for Driouech's first.
That goal prompted droves of Liverpool fans to head for the exits and their biggest concern now seems to be just how their side are going to turn this around.
There have been questions over line-ups, formations, heart and desire and whether Slot has what it takes to restore confidence to what was once a glorious winning machine and feared by all.
With his players booed off at the end of this dispiriting loss, Slot will have to find the answers soon.
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