10 of the most shocking defeats for English clubs in the Champions League

Finnbogasson Arsenal

The group stage offers wriggle room for error – but these Premier League sides’ records were still blemished by defeats they’d rather forget...

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Spartak Moscow 4-1 Arsenal – November 22, 2000

Arsenal’s record away to Eastern European opposition during their first few years in the Champions League didn’t make for particularly enjoyable reading.

After losing to Dynamo Kiev in their debut campaign, they were then beaten 3-0 by Shakhtar Donetsk on their way to the second group stage in 2000/01. Once there, Spartak Moscow inflicted yet more pain.

Sylvinho thought he’d set Arsenal on their way, giving them the lead within two minutes, and Nwankwo Kanu should have doubled it shortly after. A poor pitch and sub-zero conditions can’t have helped Arsene Wenger’s side, but once the Russians got started they couldn’t be stopped. Goals from Yegor Titov and Robson added to Marcao’s earlier brace.

Arsenal still made it through by virtue of their head-to-head record against Lyon, but crashed out to eventual finalists Valencia on away goals in the quarter-finals.

Arsenal 1-2 Auxerre – October 22, 2002

In his early years as Arsenal manager, Arsene Wenger successfully plundered the French market for some outstanding players. Indeed, five were on show for his side as Auxerre proved that Ligue 1 still had plenty of its own talent to call on – a thumping Olivier Kapo strike and a smart finish from Khalilou Fadiga gave them an unassailable first-half lead.

Arsenal pulled a goal back after the break, but even the returning Robert Pires couldn’t find a way through to deny the visitors a deserved win. Several of the Auxerre team, including both goalscorers and centre back Jean-Alain Boumsong, played in the Premier League later on in their careers.

Still, the Gunners topped their group while Auxerre crashed out – but second group stage pain awaited them after just one win from six matches.  

Maccabi Haifa 3-0 Manchester United – October 29, 2002

Despite falling behind in their home match against the same opponents, Manchester United had gone on to dismantle Maccabi Haifa with relative ease, winning 5-2.

By the time they travelled to Israel for the fifth game of the first group stage, Alex Ferguson’s side were on maximum points and had already secured a place in the top two.

With the freedom to rest players, several changes were made. The substitutes’ bench was remarkably inexperienced but the starting line-up still featured Rio Ferdinand, the Neville brothers, Paul Scholes and Ole Gunnar Solskjaer. Unfortunately, Spanish goalkeeper Ricardo – making his full debut for the club – had a night to forget. After being beaten by two impressive long-range strikes, he gave away a penalty which future Prem star Yakubu converted to complete the scoring.

Chelsea 0-2 Besiktas – October 1, 2003

Securing fourth spot and a place in the Champions League on the final day of the 2002/03 season turned out to be a defining moment in Chelsea’s history. Roman Abramovich bought the club that summer and embarked on the first of many lavish spending sprees that would turn the Blues into contenders at home and abroad.

Besiktas proved that there was still much work to be done, however, as they inflicted a humbling defeat on Claudio Ranieri’s men. Five new signings were in the starting line-up but they failed to prevent Sergen Yalcin scoring a quickfire brace for the Turkish side.

All three changes had been made by the start of the second half to liven things up, but even an Ilhan Mansiz red card after 50 minutes couldn’t gift Chelsea a way back into the game.

The Blues still finished top of Group G after notable wins at Besiktas and Lazio, and made it all the way to the semi-finals… where they lost to losing finalists Monaco 5-3 on aggregate.    

Liverpool 0-1 AK Graz – August 24, 2004

A Champions League journey that ended with that unforgettable night in Istanbul came perilously close to being cut short on a couple of occasions.

Everyone remembers the Steven Gerrard-inspired comeback against Olympiakos that resurrected Liverpool’s hopes, but rather less attention has been devoted to their struggles against Graz.

The Austrian club arrived at Anfield for the second leg of the third qualifying round with a two-goal deficit to overturn – and very nearly did so. Expecting an easy night, Rafa Benitez made three changes and his team almost paid the price for a complacent display. Mario Tokic put Graz ahead early in the second half and could have taken the game to extra-time with a little more guile.