Beaten 4-1 at home by a mightily impressive Bayern Munich side, Juventus tumbled out of the UEFA Champions League on Tuesday evening and will now join fellow fallen giants Liverpool in the UEFA Europa League.

Three sides who made sure of their places in the last 16 were CSKA Moscow, Real Madrid and AC Milan. They join Arsenal, Bordeaux, Chelsea, Fiorentina, Lyon, Manchester United, Porto and Sevilla in the draw for the first knockout round, with the final four places being decided on Wednesday evening.

The results

Group A
Juventus 1-4 Bayern Munich
Maccabi Haifa 0-1 Bordeaux

Group B
Besiktas 1-2 CSKA Moscow
Wolfsburg 1-3 Manchester United

Group C
Zurich 1-1 AC Milan
Marseille 1-3 Real Madrid

Group D
Chelsea 2-2 APOEL Nicosia
Atletico Madrid 0-3 Porto

The big game
Juventus 1-4 Bayern Munich
Goals: David Trezeguet 18 (Juventus); Hans-Jorg Butt 30 pen, Ivica Olic 52, Mario Gomez 83 and Anatoliy Tymoshchuk 90 (Bayern Munich)

Led by the sublime Olic, Bayern produced their best performance of the season to outclass Juventus in all departments, and that after the Italians had taken the lead against the run of play through a superb Trezeguet volley. Goalkeeper Butt levelled the score from the penalty spot, with the Germans taking control after the break as Juve began to feel the effects of Saturday’s energy-sapping league win over Inter. Centre-half Daniel van Buyten caused mayhem in the Bianconeri box to set up Olic for Bayern’s second. The Belgian then repeated the trick from another free-kick to allow Gomez to put the Germans two goals clear. Tymoshchuk completed the rout in the closing seconds with a cleanly struck drive from the edge of the box.

The surprise
Zurich 1-1 AC Milan
Goals: Milan Gajic 29 (Zurich); Ronaldinho 64 pen (Milan)

1-0 winners at the San Siro in the first meeting between the sides, Zurich once again gave the aristocratic Italians an uncomfortable evening. And once again the Swiss went ahead, this time courtesy of a fine Gajic free-kick from 20 metres out. The visitors eventually roused themselves from their lethargy, however, with Ronaldinho pulling them level from the spot after Alain Rochat was sent off for a professional foul inside the box.

The other games
Unbeaten Bordeaux collected their fifth win in Group A when a much-changed side saw off Maccabi Haifa 1-0 in Israel. The result ended a miserable campaign for the hosts, who failed to score or collect a single point in the section, a first for the UEFA Champions League.

Injury-hit Manchester United made sure of top spot in Group B when they beat Wolfsburg 3-1 in Germany, all the English champions’ goals coming from Michael Owen. That result allowed CSKA Moscow to snatch second place from the Germans courtesy of a 2-1 triumph in Istanbul. Milos Krasic and Evgeni Aldonin were the goal heroes for the Russians as they secured a decisive win over Besiktas in a hugely entertaining game.

Real Madrid took advantage of Milan’s draw in Switzerland to claim first place in Group C with a 3-1 victory in Marseille. Cristiano Ronaldo set the Spaniards on their way with a trademark dipping free-kick after only five minutes only for Lucho Gonzalez to equalise for the home side shortly afterwards. With an hour on the clock, central defender Raul Albiol put Los Merengues back in front with a low drive. And after Lucho had spurned a chance to bring the Frenchmen level again from the penalty spot, the irrepressible Ronaldo sealed the points with a smart finish ten minutes from time, underlining his importance to the Real cause.

Despite finishing bottom of Group D, APOEL Nicosia stole the show with an excellent 2-2 draw at Stamford Bridge, Nenad Mirosavljevic slotting home the Cypriot side’s equaliser three minutes from the end. Stunned by APOEL’s early opener, the Londoners hit back with a brace of stunning strikes from Michael Essien and Didier Drogba as they ended the group phase unbeaten. Porto, who had long since made sure of second place, eased to a 3-0 away win over Atletico Madrid, who finished level on points with APOEL but go forward to the UEFA Europa League thanks to the 1-1 draw they secured in the Cypriot capital last month.

The stat
42 - The number of months since David Trezeguet’s previous goal in the competition. The fourth-highest scorer in Juventus’s history with 167 goals, the France international last struck in the UEFA Champions League on 7 March 2006 against Werder Bremen.

Goal of the night
Besiktas 0-1 CSKA Moscow (Milos Krasic, 10)
Leading a rapid counter-attack, Alan Dzagoev slipped the ball out to a speeding Krasic on the left. The Serb’s pace took him round the back of the Besiktas defence and into the penalty box, where he fired an angled right-footed drive across goalkeeper Rustu Recber and into the top corner of the net.

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