Liverpool 1 Fiorentina 2
The Reds crashed 2-1 to a stoppage time goal from Alberto Gilardino after taking a first-half lead through Yossi Benayoun, just as they did when the French outfit travelled to Anfield in October.
The match did provide a chance for summer acquisition Alberto Aquilani to make his full debut for Rafael Benitez's side, but the Italy international faded after a bright start.
Fiorentina controlled much of the first half and almost went in front just after the half-hour mark. Direct from a corner, Lorenzo De Silvestri powered a header which he believed to be heading in the back of the net, only for it to be directed straight at Diego Cavalieri who tipped the ball over the bar.
As the half wore on, the quality dwindled and by the time the opener came in the 43rd minute, many inside Anfield had already made their way to concourses for an early half-time tea break.
Steven Gerrard's sheer persistence on the right flank won his side a free-kick which he dusted himself off to take.
Just 25 yards out, the skipper bent in a ball which found the unmarked Benayoun's run and the Israeli glanced the ball beyond Sebastien Frey and presented the goalkeeper with his only notable task of the night - picking the ball out of the back of the net.
The Viola drew level out of the blue just after the hour-mark with the type of break which troubled an unfamiliar Liverpool back four throughout the evening. Martin Jorgensen finished a flowing move when unmarked inside the area, with a powerful low strike which proved too good for Cavalieri.
The second half did produce better football from the home side, but even the introduction of the fit-again Fernando Torres for the final 25 minutes could not muster together a piece of play to force a decisive second goal.
A series of air-shots, near-misses and a flurry of corners from Liverpool ensued, until Italy international Gilardino settled the match in the second minute of injury time.
Substitute Juan Vargas robbed young defender Stephen Darby of possession before darting down the left flank and squaring for the former AC Milan striker, who calmly stroked the ball past the helpless Cavalieri, handing the Serie A outfit top spot in the group and a potentially easier draw in the knockout stages.