Arsenal's Olympiacos shambles was one of the worst nights of Arsene Wenger's reign

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Arsene Wenger's side have a poor record in Europe's biggest competition
Gunners have qualified for Champions League 19 times, but never won it
Olympiacos defeat is third time they have conceded three times at home in the competition in last 12 months
We look back at 10 times Arsenal have let their fans down in Europe
Champions League 2015-16: Latest news, results, fixtures and highlights

Published: 05:34 EST, 30 September 2015 | Updated: 11:11 EST, 30 September 2015

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Arsenal's defeat by Olympiacos on Tuesday night sees them on the brink of Champions League elimination, without a point from two games.

But as well as the disappointment that rippled around the Emirates - half-empty by the final whistle - there was an air of resigned expectancy.

In recent years Arsenal have let their fans down in Europe with increasing predictability.

Sportsmail looks back at 10 of the worst European nights under Arsene Wenger.

A dejected Arsene Wenger watches on between Steve Bould and Per Mertesacker in the Olympiacos defeat

10. Arsenal 0-1 Lens November 1998

Wenger may have hit the ground running in domestic football, but in Europe he made the slowest of starts to life at Arsenal.

After being knocked out of the UEFA Cup by PAOK Salonika in his first full season, the Gunners made it to the Champions League courtesy of the League and Cup double.

But the adventure was shortlived, a defeat away to Dynamo Kiev followed up by another at home to Lens.

Mickael Debeve's goal put Arsenal out, despite the fact that they won their final group game. Had they beaten Lens, the chances are they would have qualified for the second round at the expense of Manchester United (six group winners and two best runners-up progressed) who would go on to win it.

Lens knocked Arsenal out of their first Champions League adventure thanks to a Michael Debeve goal

The Gunners, playing their home games at Wembley, made a slow start to life in Europe's top competition

9. Arsenal 3-3 Anderlecht November 2014

Of all the poor nights Arsenal have had in Europe, this one probably mattered the least. Wenger's side still made it out of the group, and were handed a winnable second-round tie.

But the mental fragility it demonstrated, and the way it sparked panic, sees it included in this list of nights the team have let their fans down in Europe.

Three goals up at home, an injury to Mikel Arteta sparked a collapse that saw Anthony Vanden Borre - a man who couldn't hold down a place in a relegated Portsmouth defence - score twice.

If it hadn't been quite so sad it would have been funny.

Antony Vanden Borre scores his first goal, sparking an Anderlecht comeback that shocked the Emirates

8. Arsenal 1-3 Bayern Munich February 2013

There was no shame in losing to this Bayern side, one of the best in Europe and eventual winners that season, but the manner of this defeat was a problem.

The space Toni Kroos was allowed for his first goal was absurd, the second goal sloppy defending from a corner, and then, once Arsenal had got themselves back in the tie (a theme), the naivety to let Bayern score a crucial third on the break was appalling.

That third goal meant that even a 2-0 win at the Allianz Arena was not enough.

Toni Kroos celebrates after putting Bayern Munich ahead early on in a devastating defeat for Arsenal

Arsene Wenger cannot watch as his team are pulled apart by one of the best in world football

7. Arsenal 0-3 Inter September 2003

The 2003-04 season is the greatest in the history of Arsenal, but for some reason the Invincibles could not recreate their domestic dominance in Europe.

Against an Inter team which had fallen from its peak, Arsenal found themselves three goals down before half-time. Naming the goalscorers, Julio Cruz, Andy van der Meyde and Obafemi Martins, puts into context just how poor a performance this was.

However, Wenger's side did bounce back, trouncing the same side 5-1 at the San Siro in the reverse fixture.

Fabio Cannavaro and Francesco Toldo celebrate after Thierry Henry had missed a penalty at Highbury

Sol Campbell could not believe what he was seeing as Arsenal's Invincibles went 3-0 down before half-time

6. Arsenal 1-1 PSV March 2007

No sensible fan could think that losing in the final in 2006 was letting them down, against a Barcelona side that would go on to dominate Europe for a decade.

But to exit in the last 16 a year later, to a team as unfancied as PSV, was little short of shocking.

A goal down from the first leg, Arsenal got back on track when Alex - the defender who would go on to be a Chelsea star - put through his own goal.

The joy was short-lived, however, as the Brazilian defender then popped up with a goal at the right end to dump the Gunners out.

5. Arsenal 2-3 Olympiacos September 2015

For the third time in a year Arsenal conceded three goals at home in the Champions League to a team they would have expected to beat comfortably.

Defensive errors, a goalkeeping howler, and a goal conceded moments after getting back in the game - all familiar sights for an angry Emirates crowd.

Wenger had described the game as 'must win', but then selected his second-choice goalkeeper in David Ospina, who let him down badly.

The result jeopardises Arsenal's chances of getting out of the group stages, something they have managed every season since 2000 and brings added pressure on the manager from an already dissatisfied fanbase.

David Ospina drops the ball over his own goal line under no pressure, in a devastating defeat by Olympiacos

Gabriel (left) and Alex Oxlade-Chamberlain trudge off after a defeat that leaves Arsenal on the brink

4. Arsenal 1-3 Monaco February 2015

So many themes run through this defeat that it is almost impossible to mention them all.

Dominant in possession but wasteful in front of goal, Arsenal were punished on the counter attack by a Monaco side there for the taking.

And yet, when Alex Oxlade-Chamberlain got them back in the game, the tie was still winnable. Barely 60 seconds later Monaco were two ahead again, as Arsenal switched off moments after scoring.

They beat Monaco 2-0 away from home, but that third away goal cost them a place in the last eight.

Former Tottenham and Manchester United striker Dimitar Berbatov celebrates scoring for Monaco

Arsenal look dejected after conceding a third, just moments after getting back into the game against Monaco

3. AC Milan 4-0 Arsenal 2012

On paper this Milan side, featuring Thiago Silva, Marc van Bommel, Clarence Seedorf, Robinho and Zlatan Ibrahimovic looks quite impressive.

In reality they were a mish-mash of players, few of whom were at their peak, finished second in a week Serie A, were trounced at home by Barcelona in the semi-final and even allowed Arsenal to win 3-0 in the return.

But at the San Siro Arsenal capitulated, leaking four goals in calamitous fashion and all but crashing out of a two-legged tie on the night.

Thierry Henry, in his second spell at the club, was not able to stop the rot as Arsenal were thrashed by Milan

Zlatan Ibrahimovic celebrates his penalty to make it 4-0 as Arsenal were humiliated in the San Siro

2. Arsenal 1-3 Manchester United May 2009

It may be harsh to talk of losing a Champions League semi-final to a team boasting Wayne Rooney, Cristiano Ronaldo and Carlos Tevez as 'letting the fans down', but the manner of this defeat was appalling.

Behind, but still in touch after the first leg, the dream was ended after 11 minutes, when Park Ji-sung and Ronaldo had scored.

United ripped Arsenal to shreds on the break and the Emirates, which had started the night as a cauldron of noise, ended it with a quiet, embarrassed growl of discontent.

As an individual game, combining shocking defending, a collapse in the wake of great expectations and defeat to a major rival, this was hard to stomach for Guuners.

It remains Arsenal's last Champions League semi-final.

Park Ji-sung takes advantage of a Kieran Gibbs slip to put Manchester United in complete control of the tie

Cristiano Ronaldo celebrates as Arsenal were ripped to shreds by United's counter-attacking football

1. Arsenal 1-2 Chelsea April 2004

Forget the final defeat to Barcelona two years later, this is the one that really hurts for Arsenal fans.

The greatest team the club ever produced, in a year that European football stood aside and said anyone can win it, and Arsenal were put out by a late Wayne Bridge goal, and London rivals Chelsea.

With Monaco and then Porto waiting in the semis and final, and a 1-1 draw secured at Stamford Bridge, Arsenal fans rightly expected a first European Cup. But Bridge's strike ended that dream.