Arsenal manager Arsene Wenger reached an unsavory mile-stone last night in the 2-0 defeat to Bayern Munich, as Wojciech Szczęsny became the 100th Gunners player to be sent off under the Frenchman.

Arsenal’s 100 red cards range from the violent to the down-right absurd, with some dismissals, such as Szczęsny’s last night, crippling the Gunners beyond repair, and consigning them to an almost certain defeat.

Lets take a look back at some of the most contentious, infamous, and critical dismissals in the almost two decade reign of Arsene Wenger:

4. Patrick Vieira vs West Ham, Premier League, 03/10/99

‘Big V’ makes up a tenth of the total of Gunners players dismissed under Wenger, the most of any player on the list, with the Frenchman’s disciplinary problems a feature of his stay in North London.

One of the all-time great central midfielders of the Premier League, Vieira struggled to keep his head at times, with his sending off against West Ham a prime example.

The Arsenal man was dismissed for a second bookable offense after a particularly scything challenge, but matters took a turn for the worse thanks to the ever-affable Neil Ruddock, who goaded the Frenchman as he made his way off.

Vieira took exception to Ruddock’s brand of ‘farewell’, and not only shoved him in the face, but launched a blob of spit at the defender, not unlike the unpleasant dinosaur in Jurassic Park.

3. Emmanuel Adebaoyor and Kolo Toure vs Chelsea, Carling Cup, 25/02/07

The ‘Snarling Cup Final’ as we know it now, Chelsea’s fight with Arsenal close to the end of the game is one of the most iconic moments between the clubs, with tempers flaring beyond the point of reasonable control.

Jose Mourinho took it upon himself to march into the throng, with Wenger not too far behind, as the likes of Cesc Fabregas, Frank Lampard, Emmanuel Eboue and Kolo Toure laid waste to the match as a professional spectacle.

Yet it was poor Adebayor that was given his marching orders, along with Toure, and it didn’t half tick him off!

Writhing and raving, the Togolese striker took an age to leave the pitch, but with only nine Arsenal players left against the ten of Chelsea deep, into injury time, there was to be no silverware for the Gunners.

2. Jens Lehmann vs Barcelona, Champions League, 17/05/06

Underdogs Arsenal started the 2007 Champions League final with real intent, and had it not been for the first half sending off of German keeper ‘Crazy’ Jens Lehmann, they could well have brought back the trophy to London for the first time.

Clipping Barca striker Samuel Eto’o as he came charging out of his goal, the ball was actually turned in by Ludovic Giuly, but the referee pulled the game back, sent Lehmann off, and awarded Barca a free-kick. Not even 20 minutes had past.

Ronaldinho missed the target with his effort, and fans of both sides wished the referee had allowed play to continue, with Barca given a goal, and Lehmann given a booking for his poor challenge on Eto’o.

Despite Arsenal’s valiant display, where they lead for most of the match thanks to Sol Campbell’s thumping header, Barca finally made the man advantage count, scoring twice at the death to take the trophy back to Catalonia.

1. Robin van Persie vs Barcelona, Champions League, 08/03/11

Certainly the most contentious of all on this list, Arsenal’s Dutch maestro was dismissed for a second yellow for booting the ball into the net after the whistle had gone.

Crucially, Van Persie claimed he couldn’t hear a thing! The Nou Camp is no library, and with the many thousands of vociferous Barca and Arsenal fans screaming their lungs out, it is wholly believable that the striker was effectively deaf to the sounds of the ref’s piddly whistle.

Arsenal lost the game 3-1, crashing out of the Champions League 4-3 on aggregate. Without the threat of Van Persie up top, moreover playing Barca once again a man short, arguably sealed the Gunners’ fate. A truly terrible decision.

What do you think Any I’ve missed Let me know in the comments below…