Arsene Wenger’s 20 Worst Defeats as Arsenal Manager

Arsene Wenger’s 20 Worst Defeats as Arsenal Manager

“The Professor” has seen his team through some great highs and lows. All these losses had a different impact on the club and brought up questions about the past, present and future of his career at the club and the club itself.

Some results had a direct impact on the team’s chance at silverware, and others made fans, critics and maybe even some players question the Frenchman’s methods.

In chronological order, here are the 20 worst defeats in Arsene Wenger’s Arsenal career.

Champions League: Arsenal vs. Lens November 1998 1-0 Loss

Arsenal had some pretty poor performances in the Champions League during Arsene Wenger’s first season.

The loss was at home against a Lens side that finished on the same points as Arsenal, but went through because they won the head-to-head battle.

Premier League: Leeds United vs. Arsenal May 1999 1-0 Loss
2 OF 20
A Jimmy Floyd Hasselbaink goal in this fixture effectively ended Arsenal’s Premier League title hopes as the team ended the season a mere point behind Manchester United.

Arsenal’s aforementioned poor performance in the Champions League—and its departure from both domestic knockout tournaments—made this defeat even more agonizing.

UEFA Cup Final May 2000: Galatasaray vs. Arsenal Loss on Penalties
3 OF 20
A European trophy still eludes Arsene Wenger, and you have to say his first crack at one was probably his best.

It certainly isn’t shameful to lose to a Galatasaray team that included Gheorghe Hagi and Hakan Sukur, but when the former gets sent off in extra time, you would think Arsenal would end up with a win.

Missing two penalties didn’t help either.

Premier League February 2001: Manchester United vs. Arsenal 6-1 Loss
4 OF 20
Manchester United put to rest any doubt who was the boss in England at the time when they hammered Arsenal at Old Trafford.

I remember this game and how sick I felt seeing Manchester United score goal after goal. Arsenal title hopes were ended ruthlessly in this game.

FA Cup Final May 2001: Arsenal vs. Liverpool 2-1 Loss
5 OF 20
I really despised Michael Owen after this defeat. This is another game I remember all too well. Arsenal really had no right to lose after Fredrik Ljungberg put the team ahead, but that’s exactly what happened.

Arsene Wenger’s career at Arsenal hadn’t gotten off to the greatest of starts with three straight trophy-less seasons amidst some very close calls.

Premier League May 2003: Arsenal vs. Leeds 3-2 Loss
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After achieving the double in the previous season, Arsenal faltered at the last step in a bid to repeat the feat.

Leeds were again the enemy, and this time it was Mark Viduka playing the main villain.

Arsenal was leading the title race the majority of the season before three draws—coupled with the loss to Leeds—handed Manchester United the title.

Champions League Final May 2006: Barcelona vs. Arsenal 2-1 Loss
7 OF 20
Arsenal put up good fight in this game despite spending over 70 minutes with only 10 men. Still, you could say that the impact of that loss is still being felt today.

If Arsenal won, then maybe Thierry Henry would have stayed or other stars would have been more interested in joining the club.

If someone only had a time machine.

Champions League February 2007: PSV vs. Arsenal 1-0 Loss
8 OF 20
Arsenal really shouldn’t have lost this game in the away leg—they were certainly the better team on paper and should have been able to progress.

Things weren’t any better in the second leg at home as they allowed PSV to score an away goal.

Again, the impact of this loss cannot be overlooked. Arsenal could have at least made the semifinals of this Champions League. Liverpool were PSV’s next opponents and they dealt with the Dutch club easily before meeting Chelsea in the semifinals.

Arsenal could have at least gotten past Liverpool.

Carling Cup January 2008: Tottenham vs. Arsenal 5-1 Loss
9 OF 20
Tottenham fans had a lot to cheer about on this day. Spurs had not beaten Arsenal for quite a while and this performance certainly helped erase some of their memories.

It was the exact opposite for Arsenal, Arsene Wenger and Arsenal fans. The loss was even more important as there was a Carling Cup final up for grabs.

Carling Cup December 2008: Burnley vs. Arsenal 2-0 Loss
10 OF 20
After a youthful Arsenal swept aside Sheffield United and Wigan at home, there were high expectations for them to continue the run against Burnley.

It was certainly supposed to be a tougher game away from home, but the youngsters were unable to overcome their opponents. They fell behind early and did not have the fortitude to get themselves back in the game.

It wasn’t an enormous defeat, but another indicator that experience is necessary.

Champions League May 2009: Arsenal vs. Manchester United 3-1 Loss
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Arsenal failed again near the final hurdle in a European competition. Arsenal only had to score two goals and keep a clean sheet to progress to the 2009 Champions League final.

Instead, the team gave Manchester United a place in the finals by conceding two goals inside the first 15 minutes.

The first goal was a result of an unfortunate slip from Kieran Gibbs, but apart from that, the overall performance was not good enough to get the required result.

FA Cup January 2010: Stoke City vs. Arsenal 3-1 Loss
12 OF 20
In 2009/10, Arsenal did not make much progress in a competition that Arsene Wenger usually does well in.

The Gunners had just barely beaten West Ham in the previous round and faced another tough test against Stoke City. They fell behind early and equalized, but did not do much else and eventually conceded two late goals.

Arsenal really should have won that game, and the team’s lack of winning mentality was a big reason why.

Champions League April 2010: Barcelona vs. Arsenal 4-1 Loss
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The tie was basically already over as Barcelona had already scored two away goals in the first leg. It got much worse for Arsenal in the second leg as they were subject to the Lionel Messi show.

After getting a surprise lead through Nicklas Bendtner, Lionel Messi proceeded to score a hat trick in 19 minutes before adding a fourth later on in the game.

In truth, Arsenal was playing the best club team in football, but this game again showed that Arsenal had a long way to go.

Premier League September 2010: Arsenal vs. West Bromwich Albion 3-2 Loss
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Arsene Wenger’s posture in the picture tells the whole story.

Arsenal were battered in the first 75 minutes of this game and were down 3-0 thanks to some comical defending and an inability to pry open their opposition.

Samir Nasri was only player to show any fight on the day—grabbing two goals in the last 15 minutes—but the result was already a foregone conclusion.

Premier League November 2010: Arsenal vs. Tottenham 3-2 Loss
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It was great getting up at 7:45 a.m. to watch this game when the first half was going on. That feeling changed in the second half though.

Arsenal were up by two and in complete control of proceedings. By the end of the 90 minutes, the score read 3-2 Tottenham.

There is no reasonable explanation as to why that happened, but it did.

Champions League November 2010: Braga vs. Arsenal 2-0 Loss
16 OF 20
No offense to Braga, but Arsenal really should have won that game. As it stands, the Gunners were on the brink of European elimination after this defeat.

Arsenal eventually went through, but in terms of reputation, this loss had to sting.

Carling Cup Final February 2011: Birmingham City vs. Arsenal 2-1 Loss
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Um. Yeah.

There really isn’t too much to be said about this game, so we’ll just move on.

Premier League August 2011: Manchester United vs. Arsenal 8-2 Loss
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Manchester United laid it on this game. The 6-1 loss back in 2001 isn’t easily forgettable, and neither will this one be.

Arsenal has recovered—somewhat—this season, but this was definitely a horrible defeat.

Champions League February 2012: AC Milan vs. Arsenal 4-0 Loss
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This is by far Arsenal’s worst performance in Europe and showed everything wrong with the Gunners at the moment.

Mark van Bommel says the tie isn’t over, but he’s just being nice. If this result didn’t worry anyone, the next one certainly did.

FA Cup February 2012: Sunderland vs. Arsenal 2-0 Loss
20 OF 20
Arsene Wenger has seen his team drop out of three tournaments this season. You would have hoped for or expected some more fight or strength from the Arsenal squad after what happened during the week.

None of that happened, and it’s down to the players and the manager.

This loss ensures a seventh straight season without silverware.