Udinese will be the sole Italian representative in the UEFA Cup last 16 as AC Milan, Fiorentina and Sampdoria were all knocked out.
Werder Bremen's stunning second-half comeback saw favourites Milan crash out on the away goals rule at the San Siro, while Fiorentina were left heartbroken after a late winner for Ajax and a weakened Sampdoria side were dumped out after being beaten away to Metalist Kharkiv in their second leg tie.
That only leaves Udinese flying the Italian flag in the UEFA Cup this season, although they made hard work of it against Lech Poznan.
AC MILAN 2-2 WERDER BREMEN
3-3 on aggregate, Werder Bremen go through on the away-goals rule
Claudio Pizarro masterminded a dramatic Werder Bremen turnaround at the San Siro, beating Nelson Dida with two second-half headers to send favourites AC Milan crashing out of the UEFA Cup on the away-goals rule. Having drawn 1-1 in the first leg in Germany, first-half goals from Andrea Pirlo and Alexandre Pato looked to have smoothed Milan's path to the Round of 16, but it will be the German side who play Saint-Etienne in the next round after Pizarro atoned for an early miss with two goals in the second half to dump Carlo Ancelotti's side out of the competition and pile more pressure on the Rossoneri boss.
AJAX 1-1 FIORENTINA
Ajax win 2-1 on aggregate
Ajax substitute Leonardo came on to conjure an 88th-minute equaliser against Fiorentina which sent the Dutch giants through to a Round of 16 meeting with Marseille. Having taken a slender 1-0 lead into the game, Ajax trailed to Alberto Gilardino's second-half strike and were facing extra time and penalties before Leonardo rifled home the decisive goal. The winning goal was a massive blow for Cesare Prandelli's side who dominated the match and created numerous chances throughout the night.
UDINESE 2-1 LECH POZNAN
Udinese win 4-3 on aggregate
Second-half goals from Simone Pepe and Antonio Di Natale secured Udinese's place in the last 16 as Pasquale Marino's side survived a scare to overcome Lech Poznan at the Stadio Friuli. Having drawn 2-2 in Poland last week, Udinese were favourites to progress on home soil but they fell behind inside 13 minutes as Hernan Rengifo scored for Lech. The home side regained their composure, though, and after Pepe levelled just shy of the hour-mark to restore their advantage on away goals, Di Natale made sure of their passage to the next round and a meeting with holders Zenit St. Petersburg in added time.
METALIST KHARKIV 2-0 SAMPDORIA
Metalist Kharkiv win 3-0 on aggregate
Ukranian side Metalist Kharkiv eased into the Round of 16 as they added two goals to the 1-0 aggregate lead they held after last week's shock win at Sampdoria. Not tempted to sit back on their slender advantage, Metalist pushed from the start and Serhiy Valyayev and Jaja struck before the break to end a below-strength Sampdoria's hopes of progress. Metalist will now take on domestic rivals Dynamo Kiev in the next round.
UEFA CUP RESULTS
Round of 32 Second Leg
Thursday 26 February
Ajax 1-1 Fiorentina (Agg: 2-1)
CSKA Moscow 2-0 Aston Villa (Agg: 3-1)
Deportivo La Coruna 1-3 Aalborg (Agg: 1-6)
Galatasaray 4-3 Bordeaux (Agg: 4-3)
Hamburg 1-0 NEC Nijmegen (Agg: 4-0)
Manchester City 2-1 Copenhagen (Agg: 4-3)
Metalist Kharkiv 2-0 Sampdoria (Agg: 3-0)
Milan 2-2 Werder Bremen (Agg: 3-3, Bremen win on AG)
Saint-Etienne 2-1 Olympiakos (Agg: 5-2)
Standard Liege 1-1 Braga (Agg: 1-4)
Stuttgart 1-2 Zenit St. Petersburg (Agg: 2-4)
Tottenham Hotspur 1-1 Shakhtar Donetsk (Agg: 1-3)
Twente 0-1 Marseille AET (Agg: 1-1, Pens: 6-7)
Udinese 2-1 Lech Poznan (Agg: 4-3)
Valencia 2-2 Dynamo Kiev (Agg: 3-3, Kiev win on AG)
Wolfsburg 1-3 Paris Saint-Germain (Agg: 1-5)
UEFA CUP DRAW
Round of 16 First Leg
Thursday 12 March 2009
CSKA Moscow v Shakhtar Donetsk
Dynamo Kiev v Metalist Kharkiv
Hamburg v Galatasaray
Manchester City v Aalborg
Marseille v Ajax
Paris Saint-Germain v Braga
Udinese v Zenit St. Petersburg
Werder Bremen v Saint-Etienne
Round of 16 Second Leg
Wednesday 18 / Thursday 19 March 2009
Aalborg v Manchester City
Ajax v Marseille
Braga v Paris Saint-Germain
Galatasaray v Hamburg
Metalist Kharkiv v Dynamo Kiev
Saint-Etienne v Werder Bremen
Shakhtar Donetsk v CSKA Moscow
Zenit St. Petersburg v Udinese