7 of Arsenal’s Most Embarrassing European Moments

​What better way to banish the memories of another miserable European exit than to reminisce about countless other miserable European exits? Strap yourselves in Arsenal fans, this won’t be fun.

Or, strap yourselves in everyone else, this will be fun.

Fresh off the back of being dumped out of the Europa League round of 32, ​Arsenal are now facing the prospect of another season without ​Champions League football. Rubbing salt into the gaping wounds – depending how the rest of the ​Premier League season goes – they could very well be out of Europe entirely next term.

But, as supporters of the club will know, this is by no means a solitary occurrence. It’s happened worryingly often.

Here we go.

Chelsea 4-1 Arsenal – 2019/20


There’s a realisation to losing in a major final that, no matter how well you’ve played, you’ve still come second, and won nothing.

But at the very least some solace may be taken from the performance, desire and effort that is left on the park. Where, at the end, you can’t fault the team for their endeavour and can at least be proud of what they’ve achieved.

Then, there’s the 4-1 drubbing against ​Chelsea.

​Not one iota of positivity could be squeezed out of that performance. It was dire from top to bottom, manager to player, and humiliating beyond belief. Not only that, the implications it had (and still has) on the club’s future are profound.

Arsenal 1-2 Östersunds – 2017/18

Saed Kolasinac

Leading 3-0 from the first leg of this round of 32 tie, the foot was off the pedal. Against Swedish minnows Östersunds, easing up somewhat should still mean victory at the least – when you factor in the calibre of player at each club and their respective finances.

This is Arsenal we’re talking about, though. 

In the space of a single minute, what went from looking like a routine stroll into the next round grew into a genuine fear that the side haling from a tiny city in central Sweden were going to do the unthinkable. They were 2-0 up, and causing problems every time they paraded forward.

The end result would be 2-1 and the Gunners would go through, but what a damning assessment of where the club were that the defeat was celebrated like a victory. 

Bayern Munich 10-2 Arsenal – 2016/17


For the sake of agony, we’ll bunch these two matches into one beautifully packaged and combined sh*tstorm.

What still leaves irreparable scars with Arsenal fans is the promises former chief executive Ivan Gazidis made not four years prior to this drubbing. Claiming that the club would go on to ‘compete at a level like a club such as Bayern Munich’ was folly from the off, and to see the Gunners lose 5-1 twice to ​Bayern during their round of 16 Champions League clash was demoralising beyond belief.

​The mad thing is, Arsenal were 1-0 up after 45 minutes of the tie. Unfortunately, a Laurent Koscielny red card became the springboard for capitulation and, well, the rest is morbid history.

Arsenal 2-3 Olympiacos – 2015/16


Remember this lot? Arsenal fans sure do.

It was a toss-up between choosing the away defeat to Dinamo Zagreb in their first group game of the competition or this one, but this gets the nod given it was at home.

The Gunners’ qualification hopes were in tatters after just one match, but they were in dire straits after this crushing loss at home. Some shambolic defending was best laughed at to prevent the tears flowing, but Wenger’s men did pull the game back to 2-2 having found themselves twice behind.

Just as on Thursday, however, as soon as they scored, they conceded. This time, Alfreð Finnbogason was the beneficiary of some diabolical play at the back, with the 3-2 scoreline being the eventual, tear-jerking result.

Arsenal 1-3 Monaco – 2014/15

Arsenal v Monaco

There was literally no other draw that Arsenal could have got during the Champions League that season that was charitable; they were the luckiest of the lot when Monaco’s name was pulled out of the hat.

Which is why they looked like absolute trash when Monaco raced into a two-goal lead during the first leg in north London. As the injury time board was held up, a glimmer of hope emerged through Alex Oxlade-Chamberlain’s strike. It looked like a comeback was on, but no, of course, the Gunners went and conceded another with the last kick of the game. They were atrocious on the night and got what they deserved.

Heading to France for the return leg, a pair of Olivier Giroud and Aaron Ramsey goals were too little too late, and another round of 16 defeat was the result of it.

AC Milan 4-0 Arsenal – 2011/12

AC Milan's Swedish forward Zlatan Ibrahi

As soon as the ball left Kevin-Prince Boateng’s boot in the 15th minute, this tie was ended as a contest. That superb strike was the start of utter domination, in one of the darkest nights in the Gunners’ European history.

​Milan ran riot in that round of 16 clash, scoring three more time to put the tie to bed after just 90 minutes. To put it into context, it was Arsenal’s worst-ever European loss and, sadly, one fully deserved.

The hope was there of an almighty comeback when the Gunners netted three times in the first half of the return leg but, yet again, there first leg failings cost them dearly.

Arsenal 1-3 Manchester United – 2008/09

Cristiano Ronaldo

There is an argument to be made that this was more a case of ​Manchester United’s excellence as opposed to Arsenal’s failings, but still, finding themselves 3-0 down an aggregate after 11 minutes in the return home leg was not the plan.

Arsene Wenger had promised a ‘magnificent’ performance, but the gulf in class was embarrassing. Think Manny Pacquiao vs Ricky Hatton. Only worse.

Men against boys, as they say, is not what should have been the outcome of this Champions League semi-final. It was though, and it’s still a tough one for Arsenal fans to swallow. 

For more from Ross Kennerley, follow him on Twitter!  


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