Watch: 5 worst defeats of Arsene Wenger's career

Arsene Wenger
It isn’t always a good day at the office

Over the last two decades, Arsene Wenger has established himself as one of the best managers in the history of modern football. The 67-year-old, who is the longest-serving manager in Arsenal’s history, has led The Gunners to three Premier league titles and six FA Cups.

Wenger’s 20 years at Arsenal has seen more ups than downs and when he took charge in 1996, he rejuvenated the London club with his style of play.

However, Wenger has failed to lead Arsenal to European glory in spite of the fact that The Gunners have been regulars in the competition. Arsenal even had a 9-year trophy drought which came to an end after their FA Cup triumph in 2014.

The life of a manager is far from comfortable and even though Wenger has done an immaculate job at Arsenal, there were moments when his blushes could not be spared. His Arsenal team has suffered some embarrassing defeats and this piece mentions five of them.

#5 February 8, 2014 – Liverpool 5-1 Arsenal

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It was just five, but it could have been more as a rampant Liverpool side demolished Arsenal and was up by four goals inside the first 20 minutes. Arsenal, who went into the fixture top of the Premier League table, were no match for The Reds.

Martin Skrtel got on the end of two Steven Gerrard set-pieces in the first and ninth minute. Raheem Sterling scored the third goal and Philippe Coutinho’s beautiful pass set up Daniel Sturridge for the fourth. Arsenal were shocked and humiliated as they found themselves trailing by four goals at half-time.

Raheem Sterling, who was the man of the match, scored again early in the second half to make it 5-0 to the hosts. Mikel Arteta converted a penalty in the 69th minute after Alex Oxlade-Chamberlain was brought down. It wasn’t even a consolation goal as the day was one to forget for Arsene Wenger and his team.

#4 February 25, 2001 – Manchester United 6-1 Arsenal

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Old Trafford witnessed a footballing masterclass from the hosts as they brushed aside The Gunners. The victory meant that United had a 16 point lead at the top of the table with only 10 games left at that point in the season.

Arsenal, who needed to win the contest to have any hopes of winning the Premier League, saw their hopes shattered courtesy of a magnificent United display. The Red Devils took the lead as early in the second minute as Dwight Yorke opened the scoring.

Theirry Henry levelled the score after some good build up play, but Yorke scored again on the 17th and 22nd minute. He then set up Roy Keane for United’s fourth and Ole Gunnar Solskjaer joined the party when he scored United’s fifth of the afternoon in the 37th minute. Teddy Sheringham got his name on the scoresheet in the 90th minute and that was the icing on the cake.

Sir Alex Ferguson had a wide smile on his face at the end of the match and for Wenger, it was a day to forget.

#3 January 22, 2008 – Tottenham Hotspur 5-1 Arsenal

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Tottenham went into this game seeking the first win over their arch-rivals in nine years and a place in the Carling Cup final. The first leg finished 1-1 after Theo Walcott scored in the 79th minute to cancel out Jermaine Jenas’s opener.

The match had a start that Spurs fans would have dreamed of as Jermaine Jenas scored in the 4th minute. Things got even better for the hosts as Nicklas Bendtner scored an own goal that gifted Spurs a two goal cushion. Robbie Keane made it 3-0 shortly after the break and Aaron Lennon scored an emphatic fourth on the hour mark.

Emmanuel Adebayor pulled a goal back in the 70th minute but it was too little too late and Steed Malbranque’s 90th-minute goal completed Arsenal’s misery. The Gunners were frustrated to the core and a heated up argument between Bendtner and Adebayor during the match just summed it up.

#2 February 27, 2011 – Birmingham City 2-1 Arsenal

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Alex McLeish and his team knew the obvious that they were the underdogs in the final. Winning this match and subsequently ending the club’s 48-year long wait for a trophy was easier said than done. Arsenal, who were having a six-year trophy drought of their own saw this as the ideal opportunity to end it. However, things didn’t turn out to be the way the Gunners would have expected.

Arsenal, who were without Cesc Fabregas and Theo Walcott due to injury, found themselves trailing after 28 minutes as Nikola Zigic headed in Sebastian Larsson’s corner. Arsenal were nervous, complacent and shaky and on the other hand, Birmingham were playing with flair and confidence.

Robin van Persie equalised in the 39th minute but his failed side to score another as Ben Foster was in fine form and he pulled off some magnificent saves. Extra time looked a certainty before a horrendous mix-up between Laurent Koscielny and Wojciech Szczesny gifted Obafemi Martins a golden chance in the 89th minute.

Birmingham defeated Arsenal against all the odds and the day that was supposed to end in jubilation for Wenger and his team, ended in humiliation.

#1 August 28, 2011 – Manchester United 8-2 Arsenal

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The worst defeat in the club’s history for more than a century, this 8-2 drubbing put serious question marks over Wenger’s future at the club. Arsenal were still recovering from the loss of Cesc Fabregas and Samir Nasri to Barcelona and Manchester City respectively and this trip to The Theatre of Dreams came at the wrong time for them.

Danny Welbeck fired the hosts into the lead in the 22nd minute and goals from Ashley Young and Wayne Rooney made it 3-0 for United. Theo Walcott scored just before the break to make it 3-1.

Arsenal were dismantled in the second half as Wayne Rooney scored twice, Ashley Young, Nani and Ji-Sung Park completed the scoreline. Robin van Persie, who missed a penalty in the first half, managed to pull one back and Carl Jenkinson was sent off in the second half. This defeat made the weaknesses in the Arsenal squad obvious and Wenger brought in Mikel Arteta, Per Mertesacker and Alex Santos before the transfer window slammed shut.

In spite of the early setbacks, Wenger led Arsenal to a third place finish that season, but this defeat will haunt Arsenal for years to come.

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