Prior to kick-off, Manchester City seemed to be the only English team interested in progressing to the last 16 of the Uefa Cup and while Mark Hughes’ side beat FC Copenhagen to reach the next round, understrength Aston Villa and Tottenham joined David Beckham’s Milan and Spanish giants Valencia in crashing out of the competition to free-up their respective managers’ diaries.
With a Carling Cup final to look forward to, Harry Redknapp had made clear that his side’s fixture against Shakhtar was a real irritant and after losing the first leg in Ukraine 2-0, Tottenham drew 1-1 at White Hart Lane to exit the competition.
Giovani dos Santos put the North London side ahead with a fine effort but any hopes of taking the game to extra time were dashed when Fernandinho struck with four minutes remaining. Shakhtar will now face CSKA Moscow following their victory over Martin O’Neill’s Aston Villa. Report / Stats&ratings
Chasing fourth place in The Premier League, Villa surrendered their place in the Uefa Cup when a heavily-weakened team were defeated 2-0 in Russia by CSKA Moscow, sealing a 3-1 aggregate defeat for the Premier League side.
Relative unknowns Barry Bannan and Marc Albrighton earned senior debuts for Martin O’Neill’s side and, after a comfortable first half, CSKA’s class began to show after the break as Yuri Zhirkov converted following a clever free-kick routine after 61 minutes.
The 2005 Uefa Cup winners then extended their lead in the final minute when the competition’s top scorer, Vagner Love, converted on the break for his 10th goal of the campaign. Report / Stats&ratings
City, meanwhile, secured their place in the last 16 where they will face Aalborg following a 2-1 win over Copenhagen and 4-3 victory on aggregate.
Craig Bellamy struck twice (73, 80) to continue his fine form for his new club while Copenhagen claimed a last-gasp consolation thanks to Martin Vingard. Report / Stats&ratings
More Danish opposition awaits Mark Hughes’ side as Aalborg humbled Deportivo La Coruna 3-1 at the Riazor, securing a remarkable 6-1 aggregate win over the Spanish side. Sergio Gonzalez put Depor in front (38) but a three-goal blitz from Luton Shelton (38), Andreas Johansson (45) and Tomas Enevoldsen (45) put Aalborg firmly in control before half-time.
The shock of the night saw Serie A giants Milan crash out of the competition on away goals to Werder Bremen.
Following a 1-1 draw in Germany, Milan looked to be cruising towards a place in the last 16 when an Andrea Pirlo penalty (27) and a goal from Brazilian wonderkid Alexandre Pato (33) put them 3-1 up on aggregate.
But Carlo Ancelotti’s men were unprepared for a Bremen comeback inspired by on-loan Chelsea striker Claudio Pizarro who scored after 68 and 78 minutes to dump the seven-time European Cup winners out of the competition.
Bremen will face St Etienne in the last 16 after goals from Dimitri Payet (45) and Ilan Dell’Igna (58), countered by Oscar Marcos’ reply (75), saw them beat Matt Derbyshire’s Olympiacos 2-1 on the night and 5-2 on aggregate
Rivalling Milan’s exit on the Uefa Cup Richter scale was an away goals defeat for Valencia as they drew 2-2 at home with Dynamo Kiev and 3-3 on aggregate.
Artem Kravets was Valencia’s conqueror as he scored twice (34, 73), meaning goals from Carlos Marchena (45) and Asier Del Horno (54) were not enough to extend the Spanish side’s European campaign.
Dynamo will now tackle domestic rivals Metalist Kharkiv after they defeated Sampdoria 2-0 in Ukraine and 3-0 on aggregate thanks to goals from goals from Serhiy Valiyaev (30) and Jackson Coelho (40).
Martin Jol’s Hamburg were all-but guaranteed their place in the last 16 thanks to a 3-0 first leg victory over NEC Nijmegen in Holland and any hopes of a remarkable turnaround were ended after only nine minutes on Thursday night.
Croatia international Ivica Olic struck after nine minutes at the HSH Nordbank arena and the Bundesliga outfit will now face Galatasaray in the last 16 after a thrilling victory for the Turkish side against Bordeaux.
A 0-0 first leg draw in France gave no indication of the drama that was to follow in Turkey as Gala set the seal on a 4-3 victory thanks to a last minute goal from Sabri Sarioglu.
Bordeaux had gone in front after just one minute through former Manchester United forward David Bellion and while Gala responded through Arda Turan (43, 65) and Harry Kewell to go 3-1 in front, goals from Marouane Chamakh (74) and Fernando Cavenaghi (45) gave Bordeaux the lead on away goals before a dramatic conclusion to the tie.
Steve McClaren may have taken Middlesbrough to the 2006 Uefa Cup final but he was unable to repeat the trick with FC Twente after the Dutch side lost 7-6 on penalties to Marseille.
Leading 1-0 from the first leg in France, Twente fell behind to a Hatem Ben Arfa goal after 24 minutes and suffered the pain of losing on the dreaded spot-kicks.
Marseille will now tackle Ajax in the next round after the Dutch side drew 1-1 with Fiorentina, Leonardo Santiago’s 88th minute equaliser following Alberto Gilardino’s 61st-minute opener giving Ajax a 2-1 aggregate win.
Holders Zenit St Petersburg will face Udinese in the last 16 following a 2-1 win over Stuttgart which gave them a 4-2 aggregate win over the German club. Igor Semshov (42) and Victor Faitzulin (86) were on target for the Russians while Timo Gebhart (80) scored for Stuttgart.
Udinese are Zenit’s next opposition after Simone Pepe (57) and a last-minute goal from Antonio Di Natale saw them defeat Lech Poznan 2-1 on the night, 4-3 on aggregate. Hernan Rengifo (13) had taken the Polish side to within touching distance of extra time.
Paris Saint Germain secured a comfortable 5-1 aggregate victory over Wolfsburg thanks to a 3-1 win on the night in Germany.
Two goals from Guillame Hoarau handed the French side a 2-0 win in the first leg but on Thursday it was Pegguy Luyindula at the double (pen 38, 73). Jerome Rothen also netted after 60 minutes while Wolfsburg’s solitary effort came from Makoto Hasebe (63).
Their opponents in the last 16 will be Braga of Portugal who, having won the first leg on home turf 3-0, drew 1-1 with Standard Liege. Deiudonne Mbokani (79) put Standard in front before Luis Aguiar’s reply (88).
Draw for the last 16:
Werder Bremen v St Etienne
CSKA Moscow v Shakhtar Donetsk
Udinese v Zenit St Petersburg
Paris Saint Germain v Braga
Dynamo Kiev v Metalist Kharkiv
Manchester City v Aalborg
Marseille v Ajax
Hamburg v Galatasaray