UEFA Cup favourites Milan were eliminated at the last 32 stage by Werder Bremen last night with Claudio Pizarro's second-half double in a 2-2 draw putting the German side through on away goals.
After a 1-1 draw in the first leg, Andrea Pirlo put the hosts in front at the San Siro with a penalty in the 27th minute after Werder's Torsten Frings had blocked a David Beckham free-kick with his arm.
Brazilian forward Alexandre Pato doubled the lead six minutes later, rifling the ball under the bar from outside the area at the end of a superb run from just beyond halfway.
The Germans, who were well on top before the opening goal and wasted some good chances after Pato struck, hit back in the 68th minute when Pizarro nodded in a Diego free-kick.
The Peruvian used his head again to put away a cross from the left 12 minutes from time to send Werder through to the last 16.
Italy's Fiorentina were also eliminated after a 1-1 draw at Ajax, the Amsterdam outfit going through 2-1 on aggregate. Sampdoria's elimination to Ukraine's Metalist Kharkiv leaves Udinese, who ousted Lech Poznan 4-3 on aggregate, the only Serie A team left in the competition.
Udinese play holders Zenit SP in the next round. The Russians beat Stuttgart 2-1 away yesterday for a 4-2 score over the two legs.
Galatasaray scored a last-minute winner to knock out Bordeaux in a seven-goal thriller to stay on course for a UEFA Cup final in their home city of Istanbul.
Turkey defender Sabri Sarioglu struck from the edge of the penalty area to give the 2000 UEFA Cup winners a 4-3 first knockout round victory at the Ali Sami Yen stadium as Bordeaux's fine fightback from 3-1 down ended in heartbreak.
The May 20 final will be staged at the home of Galatasaray's arch-rivals Fenerbahce.
Former UEFA Cup winners CSKA Moscow took full advantage of an under-strength Aston Villa team by easing into the last 16 with a 3-1 aggregate win.
A 1-1 draw in the first leg at Villa Park left all to play for but in sub-zero temperatures in the Russian capital, the 2005 winners proved too strong in a 2-0 win.
Yuri Zhirkov scored from outside the penalty area just past the hour mark and the competition's leading scorer Vagner Love took his tally to 10 with a crisp finish in stoppage time.
Another English team, Tottenham, crashed out after being held to a 1-1 draw at home by Shakhtar Donetsk but a Craig Bellamy double ensured Manchester City provided the first significant return on their Arab owners' investment in the club by advancing to the last 16 of the UEFA Cup.
Bellamy's goals delivered a 2-1 win over FC Copenhagen and ensured Mark Hughes's team progressed 4-3 on aggregate.
Leading 2-0 from the first leg, Shakhtar only briefly looked in danger of relinquishing control of the tie after Mexican midfielder Giovani dos Santos opened the scoring ten minutes into the second half.
One more goal would have been enough for the Spurs to force extra-time but it was to be the visitors who found the net, Fernandinho grabbing a late goal to seal Shakhtar's place in the last 16.