There's meant to be no easy games in the Champions League...but some do look more inviting on paper than others.
Losing to Bayern Munich or Barcelona is eminently forgivable, but when a Premier League side with all their riches and star power go up against the bottom seed in the group, you generally expect victory.
Yet there's been plenty of examples of Premier League sides coming a cropper...
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.
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, Sir 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 Premier League star Yakubu converted to complete the scoring.
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 Olympiacos 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.
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.
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.
Some fella called 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 Olympiacos – 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 Olympiacos 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.
Red Star 2-0 Liverpool – November 6, 2018
The defeated finalists the previous season, Liverpool were given a very tough group in 2018/19 alongside PSG and Napoli. But it would be six relatively easy points against Crvena Zvezda (or Red Star Belgrade, if you're old)...right?
It was at Anfield: Liverpool ran out 4-0 winners. But it was a different story in Serbia. Jurgen Klopp would later say that Liverpool could not 'find their mojo' after watching Red Star dominate the first half, with Milan Pavkov scoring twice in the space of seven minutes.
The Reds couldn't find a response, and ended up eking through the group on goals scored. Of course, they went on to win the whole thing that season, so...
Istanbul Basaksehir 2-1 Manchester United – November 4, 2020
We probably wouldn't be massively surprised by this from Manchester United in the years to follow, but in 2020 there was still some juice to be squeezed from being stunned at how bad they could be at times.
That was especially true given United had started a very tricky group in such convincing fashion, winning 2-1 away to PSG in their opening game and then battering RB Leipzig 5-0. But it all started to go wrong in Istanbul Former Newcastle and Chelsea striker Demba Ba opened the scoring early on before Edin Visca doubled the lead for the tournament debutants.
Anthony Martial scored a quick response, but that was as much as Ole Gunnar Solskjaer's side had in reply. The defeat ultimately ended up costing United qualification to the knockouts as RB Leipzig rallied to go through in second place, putting Solskjaer's position as manager in doubt.
Young Boys 2-1 Manchester United – 14 September, 2021
Fast forward ten months, and Solskjaer is still in the United dugout having led his side to Champions League qualification again. In hindsight, he might wish he hadn't bothered.
Right in their very first game, United fell to another humiliating defeat. Things looked rosy after a newly-returned Cristiano Ronaldo gave them the early lead, but a first-half red card for Aaron Wan-Bissaka gave them a challenge as they tried to protect their lead.
They held out until the 66th minute, when Moumi Ngamaleu got an equaliser. Ah well, a point away from home with ten men isn't so ba---oh, Jordan Pefok has scored 95th minute winner. This time, Solskjaer lasted just another couple of months before United got rid.
We're not even going to bother including United's 3-2 defeat to Galatasaray in 2023, because by then it was no longer surprising.
Dinamo Zagreb 1-0 Chelsea – 6 September 2022
Not the best way to make a first impression on a new ownership, is it? The Boehly/Clearlake era had just begun at Stamford Bridge a few months before, but it did not start happily as Thomas Tuchel's side suffered a 3-0 defeat to Leeds and lost 2-1 to Southampton in August.
That put the pressure straight on the manager, and this defeat in Zagreb in his 100th game in charge of the club - courtesy of Mislav Orsic's early goal - proved to be the last straw.
Tuchel was dismissed within 24 hours, with Graham Potter immediately coming in from Brighton as his replacement. And as we all know, that just went great.
