Liverpool's mini-slump continued at Charlton as two goals late in the first half proved enough to seal a 2-0 victory for the hosts.
The Reds were looking to bounce back from last weekend's defeat at champions-elect Chelsea, and also keep the pressure on Manchester United in the race for second place.
Charlton started well but had some defending to do in the seventh minute when Steve Finnan whipped in a cross from the right. Fernando Morientes found himself in space just inside the area, but his side-footed, first-time effort was straight at Thomas Myhre.
The visitors then spurned another opportunity to take the lead on 16 minutes. Xabi Alonso swept a deep ball across the field from the left, which picked out Peter Crouch on the far side of the penalty area.
He opted to control with his chest rather than head at goal, only to then make a complete hash of the attempted shot, screwing the ball horribly wide. As the half-hour mark passed, it was still all Liverpool. Yet the visitors were unable to turn their dominance into a clear-cut chance.
On 42 minutes, a chip through from Radostin Kishishev picked out Darren Bent running into the left side of the Liverpool area. The England squad man's first touch took him away from the advancing keeper, before, under what looked minimal contact at best, he went to ground.
It was, however, enough to convince referee Andre Marriner, who pointed immediately to the penalty spot and then cautioned Dudek. Bent kept his cool to slot his 16th goal of the season, low into the left corner.
And Charlton doubled their lead in stoppage time. Smertin dashed past Sami Hyypia and to the by-line. His cross into the near post was cut out by Jamie Carragher, but Addicks skipper Young was first to the rebound, and drove a low strike through Dudek's legs.
Liverpool were quickest to settle following the restart, as they again dominated possession. It could, though, so easily have been 3-0 on 53 minutes.
It was Darren Bent who almost brought The Valley to their feet when he latched onto Young's pass and smashed the ball against the crossbar, with Dudek well beaten.
The Liverpool goal was leading a charmed life, as moments later Darren Bent got in behind the defence again, and cut the ball back for Marcus Bent - only for the former Everton man to see his low strike bounce back off the base of the post.
And when the ball did break kindly for the visitors, they could not find the target, Mohamed Sissoko drilling a low effort horribly wide with 24 minutes to go.
Morientes forced a good low save from Myhre with an angled drive, and Kishishev was on hand to hack the loose ball clear as Addicks held firm for a much-needed home win - and condemned Liverpool to a third straight away league defeat and just one point from a possible 12.
