Arne Slot saw much-changed Liverpool fall to a sixth loss in seven matches as Ismaila Sarr's clinical brace helped Crystal Palace reach the Carabao Cup quarter-finals.
Oliver Glasner's Eagles got the better of the Reds for the third time this season as they followed their Community Shield shoot-out triumph and last month's Premier League victory at Selhurst Park with an Anfield win.
Sarr's first-half brace and a late Yeremy Pino strike secured FA Cup holders Palace a 3-0 fourth round victory as increasingly scrutinised Liverpool boss Slot's bold decision to make 10 changes backfired in front of a full house.
The result continues the reigning Premier League champions' ruinous run that started with their Selhurst Park setback 32 days ago, whereas Glasner's side can dream of adding another trophy to their cabinet.
Slot's men had started Wednesday's tie brightly, only for familiar foe Sarr to score twice at the end of the opening period to make it seven goals in nine matches against Liverpool.
Palace continued to cruise through the second half. The tie was over by the time teenage Reds substitute Amara Nallo was sent off in the 79th minute, with Pino adding extra gloss late on.
Glasner made five changes compared to the 10 of Liverpool, whose debutant Kieran Morrison headed over early on before teenager Rio Ngumoha confidently cut in from the left flank and bent an effort wide.
Federico Chiesa led the line for the home side and wasted a decent opening midway through the first half, before seeing a cross-shot thwarted by Walter Benitez after more good work by 17-year-old Ngumoha.
Freddie Woodman, the boyhood Palace fan making his Liverpool bow, held Will Hughes and Sarr efforts as the visitors began to pose more problems.
That pressure, and a slice of luck, brought a 41st minute breakthrough. A heavy Daniel Munoz touch was cut out in the box by Joe Gomez, but he inadvertently teed up Sarr to slam low past Woodman in front of the Kop.
That gut punch was followed by another blow four minutes later. Sarr met a low ball through the middle with a flick to Pino, who smartly played back for the Senegal international to take a touch and guide past Woodman.
There was a defiant roar from the Liverpool faithful when the sides returned from the break, but Palace kept the hotchpotch hosts at bay.
Sarr saw an attempt at a hat-trick denied by Woodman and was replaced just after the hour mark, perhaps with Glasner expecting a tougher challenge against Brentford on Saturday.
Palace's bench was far stronger than the Reds, with Slot introducing Wellity Lucky for his debut as part of an inexperienced triple change that saw Andy Robertson, Alexis Mac Allister and Morrison withdrawn.
Nallo was among those brought on but would not finish the match after bringing down Justin Devenny as the Palace replacement ran through. It was the 18-year-old's second red card on just his second Liverpool appearance.
More pain was to follow from a Liverpool perspective as summer singing Pino showed his quality when shifting the ball onto his right and rifling home his first Palace goal in the 88th minute.
