Alberto Gilardino's stoppage time winner ensured Liverpool ended a disastrous Champions League campaign with a 2-1 defeat against Fiorentina at Anfield on Wednesday.
Yossi Benayoun's first half header had given the hosts a 43rd-minute lead against the run of play before Martin Jorgensen levelled for the Italians after half time.
And in a finish which was typical of Liverpool's lacklustre season, Gilardino struck in the dying seconds to give the Italians their second victory this season over the five-times European champions.
"It wasn't our strongest team tonight but we gave a good account of ourselves. We were a bit unlucky to lose in the end."
It was not all doom and gloom for manager Rafa Benitez as Alberto Aquilani produced an encouraging display on his long-awaited first start for the club while Fernando Torres also returned from injury.
Liverpool fans have waited four months for Aquilani to make his first start in a red shirt. But having been out for so long he is clearly going to need time before he starts repaying some of his huge transfer fee.
The Italian moved to Merseyside in August as a midfield replacement for Xabi Alonso, who joined Real Madrid.
However, he arrived while still recovering from a summer knee operation and had not started a game for his new club until now.
In what proved to be a low-key debut, Aquilani demonstrated some decent touches and clever passing without being spectacular, but Gerrard is confident he will prove to be a good signing.
"The boy's a player, there's no two ways about it," Gerrard said.
"He sees a pass, he's on the same wavelength and I have no doubts he'll turn into a fantastic player for this club." With Forentina safely through to the last 16 and Liverpool resigned to playing in the Europa League after Christmas, this was a dead rubber.
At times it seemed as though Anfield was staging a friendly as both sides showed a distinct lack of urgency, the visitors carving out the best chances before Benayoun broke the deadlock.
With nothing to play for but pride and with a titanic Premier League game against Arsenal on Sunday, Benitez used the game to give some of his fringe players a chance to shine in the Champions League spotlight.
Liverpool-born defender Stephen Darby was handed his first senior start at right-back and he was kept busy along with Diego Cavalieri, the second-choice keeper.
The hosts would have been behind at half time if Cavalieri had not produced a superb reflex save to keep out Lorenzo De Silvestri's 33rd minute header while the Brazilian also saved Daniel Agger from embarrassment after the Danish defender's weak backpass threatened to let in Mario Santana.
Cavalieri was also forced to beat away an awkward long-range effort from Riccardo Montolivo before Benayoun broke the deadlock two minutes before half time against the run of play.
It was made by Steven Gerrard. After winning a free-kick just outside the penalty area on the right, the Liverpool captain delivered a fine cross for Benayoun to head his sixth goal of the campaign.
Agger should have doubled the lead on the hour mark but, with the goal at his mercy, failed to connect with another excellent cross by Gerrard.
It was to prove a costly miss as three minutes later Jorgensen, who had earlier blazed over the bar, kept his composure to beat Cavalieri with a low finish after slack marking in by the hosts.
Fiorentina's fans were still celebrating as Torres made his long-awaited return. Liverpool's 10-goal leading scorer had missed the previous five games with a groin problem but was sent on in the 64th minute as a replacement for Dirk Kuyt.
Liverpool have missed Torres' threat in front of goal yet he was unable to inspire his team-mates to victory on this occasion.
Aquilani lasted 75 minutes before he was replaced by 18-year-old Spaniard Daniel Pacheco, who was making his first appearance for the club.
But just as the game appeared to be heading for a draw, Gilardino kept his composure to hit a dramatic winner and leave Liverpool totally deflated.
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