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.
Copenhagen 1-0 Manchester United – November 1, 2006
After several dalliances with the qualifying rounds, the 2006/07 season was Copenhagen’s first experience of the Champions League proper. Facing Manchester United at home in the fourth round of fixtures, they were without a goal, let alone a win in the competition.
That all changed when former Aston Villa striker Marcus Allback struck late in the second half, and his scrappy goal stabbed home from close range was enough to send United crashing to defeat. Cristiano Ronaldo thought he’d equalised with moments remaining, but his effort was ruled out for offside.
Not that it mattered: United still topped the group and went all the way to the semi-finals, where Milan beat them 5-3 on aggregate.
Young Boys 3-2 Tottenham – August 17, 2010
After Tottenham pipped Manchester City to the final Champions League spot, only Young Boys stood in the way of a place in the group stage. It was expected to be a relatively straightforward assignment, but Spurs toiled on a plastic pitch in the play-off first leg, going 3-0 down inside half an hour.
Although Harry Redknapp rested a couple of players for fear of them picking up injuries on the artificial surface, that was no excuse for a slow and panic-ridden start.
Fortunately, goals from Sebastien Bassong and Roman Pavlyuchenko either side of the break gave Spurs hope – and a comfortable 4-0 win back at White Hart Lane saw them progress.
Ajax 3-1 Manchester City – October 24, 2012
While Ajax were busy winning the Champions League final in 1995, Manchester City had only narrowly avoided relegation from the top flight. But much had changed in the intervening years.
As Ajax were continually picked apart by predatory clubs from wealthier leagues, Sheikh Mansour’s takeover had transformed City’s prospects overnight. They needed a win here to kick-start their Champions League campaign too, having lost to Real Madrid and drawn at home to Borussia Dortmund in their first two matches.
Things started well: Samir Nasri scored an opener against the run of play, but Ajax’s youngsters overwhelmed their far more expensively assembled opponents with a display of great energy and intent. Christian Eriksen capped a deserved win with a deflected shot which beat Joe Hart, leaving City bottom of their group and contemplating another early exit.
Chelsea 1-2 Basel – September 18, 2013
Jose Mourinho’s first Champions League game since returning to Chelsea ended in a shock defeat at Stamford Bridge. Basel were expected to offer little resistance, particularly once Oscar put the home side ahead shortly before the break, but the Swiss champions recovered well to turn the tide and claim a famous victory.
Mohamed Salah, who would also score the winner in the two sides’ next meeting a couple of months later, curled the ball past Petr Cech to equalise with 20 minutes remaining. Then Marco Streller headed in from a corner to give Basel a lead that they refused to surrender.
Mercifully for Mourinho, Chelsea recovered to win four of their remaining five matches and top the group ahead of Schalke. After knockout wins against Galatasaray and PSG they were knocked out in the semi-finals by Atletico Madrid.
Arsenal 2-3 Olympiakos – September 29, 2015
Towards the end of Arsene Wenger’s reign, the last 16 of the Champions League had begun to seem like the absolute limit of Arsenal’s European ambitions.
However, the Gunners were in serious danger of falling short of even that milestone after an embarrassing loss to Olympiakos left them pointless and bottom of their group after two games. Arsenal had met the Greek side in three of the last six seasons, winning each of their home matches and losing the away fixtures.
This, then, was not going to script. Arsenal twice pegged back their opponents through Theo Walcott and Alexis Sanchez, but Icelandic striker Alfred Finnbogason took advantage of some lax defending to score the winner.
Wenger’s men recovered to squeeze through in second place – via a 3-0 win in Piraeus – but were then thrashed 5-1 on aggregate by Barcelona.
