Liverpool 2-3 Bolton
Djorkaeff's late penalty left no way back for Liverpool
A last-minute penalty from Youri Djorkaeff helped Bolton knock Carling Cup holders Liverpool out of the competition after a dramatic match at Anfield.
Mario Jardel's early strike had put Bolton into the lead before Danny Murphy equalised for Liverpool midway through the second half.
A Jay-Jay Okocha free-kick put his side into the lead for the second time, but Liverpool again fought back from behind as Vladimir Smicer's spectacular effort with seven minutes remaining levelled the scores.
But it was not enough to deny the visitors and Salif Diao's foul on Kevin Davies gave Djorkaeff the chance to beat Jerzy Dudek from the spot and send Bolton into the quarter-finals.
Jardel punished some slack Liverpool defending as he headed home Djorkaeff's well-directed corner for his third goal for the club after just four minutes, having been left totally unmarked.
Liverpool responded with a 35-yard free-kick from John-Arne Riise which stand-in Bolton keeper Kevin Poole spilled into Smicer's path, but the midfielder blasted his effort over the bar.
Soon after, Smicer's cross from the right was clipped just over by Emile Heskey, while another fierce Riise free-kick flashed over the bar after the energetic Anthony Le Tallec won a free kick in a dangerous area.
Liverpool's first flowing attack came after 25 minutes when youngster Jon Otsemobor sprinted clear on the right, linking up with Smicer before Le Tallec's shot was blocked by Emerson Thome in the penalty box.
4 mins: Jardel puts Bolton into an early lead
70 mins: Murphy equalises for Liverpool
76 mins: Djorkaeff effort disallowed for Bolton
79 mins: Okocha puts Bolton pack into lead
85 mins; Smicer again levels the scores
90 mins: Djorkaeff seals the game for Bolton
But Bolton, looking organised and controlled in midfield, had few other problems before half time as they defended their lead.
Liverpool started well in the second period with Heskey's shot headed away from goal by Ivan Campo and El-Hadji Diouf wasting a good opportunity after good work from Murphy.
It took a good save from Dudek at Jardel's feet to stop Bolton doubling their lead on 55 minutes as the Brazilian raced onto a through ball.
On the hour, an angled effort from Riise clipped the bar as Liverpool raised the tempo.
And the Reds were rewarded for an improved display as they finally scored their equaliser on 70 minutes.
Diao's hopeful cross from the left sailed clear of the Bolton defence for Murphy to race in from the left and direct a powerful header past Poole.
Bolton thought they had regained the lead on 76 minutes when Djorkaeff forced the ball over the line after a long throw-in from Okocha was not cleared.
But after a period of indecision, referee Mike Riley ruled there had been a handball in the build-up.
Just three minutes later though, Bolton did move ahead for the second time.
Diao was penalised for a foul just outside the box and Okocha curled a perfectly-placed free-kick past Dudek.
Liverpool refused to accept defeat though, and on 85 minutes substitute Seven Gerrard fed Smicer through the middle and the Czech crashed in a superb effort from 25 yards.
And with extra time looming, Bolton launched a late attack in the 89th minute and were rewarded a penalty when Diao brought down Bolton striker Davies in the box.
Djorkaeff held his nerve to send the penalty in off a post and past Dudek to send the holders out of the Carling Cup.
Liverpool: Dudek, Otsemobor, Biscan, Traore, Riise, Diouf,
Diao, Murphy, Smicer, Heskey, Le Tallec. Subs: Kirkland, Kewell,
Gerrard, Sinama Pongolle, Cheyrou.
Bolton: Poole, Barness, N'Gotty, Thome, Gardner, Djorkaeff,
Campo, Okocha, Ba, Pedersen, Jardel. Subs: Jaaskelainen,
Charlton, Nolan, Frandsen, Davies.
Referee: M Riley (W Yorkshire)