Arsene Wenger: The Arsenal manager's worst moments

And now, the end is near. Arsene Wenger certainly did it his way at Arsenal, but his reign at the club is drawing to a close.

The Frenchman caught the footballing world by surprise on Friday by announcing he will leave the Gunners at the end of the season, ending his 22-year tenure. 

During over two decades in charge, Wenger has won the Premier League three times and lifted the FA Cup on seven occasions.

However, it hasn't always been plain sailing during his time in England. There have been near misses, painful departures and disappointing defeats.

Here, we recall five moments Wenger would probably like to forget (and that is without even mentioning his shoving match with Jose Mourinho in 2014).

THE END OF THE INVINCIBLES

Arsenal's Invincibles were unbeaten in the Premier League since May 2003 when they turned up at Old Trafford on October 24, 2004. However, after 49 games, the run came to an end in controversial circumstances.

Manchester United broke the deadlock when Ruud van Nistelrooy converted a contentious penalty awarded in the 73rd minute for a foul by Sol Campbell on Wayne Rooney, who later scored his side's second goal on his 19th birthday to wrap up a 2-0 win.

The final whistle saw the end of the action on the pitch, only for the bad blood to continue in the tunnel. There was no swapping of shirts and Campbell refused to shake Rooney's hand, despite the pair being team-mates with England.

Wenger reportedly confronted Van Nistelrooy before rival manager Alex Ferguson became involved, leading to what the media dubbed as "The Battle of the Buffet". Food was thrown in the direction of the United boss, who was forced to change before undertaking his post-match interviews.

HEARTBREAK IN PARIS

While he led Arsenal to glory domestically, Wenger has never quite managed to conquer Europe during his long time at the helm of the Gunners, although he may still bow out with Europa League success.

The closest they came to winning the Champions League was in the 2005-2006 season, as they knocked out Real Madrid, Juventus and Villarreal to set up a showdown with Barcelona in Paris.

Despite goalkeeper Jens Lehmann's early red card for bringing down Samuel Eto'o outside the penalty area, defender Campbell headed Arsenal into a 37th-minute lead.

Yet Wenger's men wasted several chances to double their lead, allowing Barcelona to rally in the closing stages. Eto'o levelled the game before Juliano Belletti grabbed the winner with 10 minutes remaining, beating replacement keeper Manuel Almunia at the near post.

THE DEPARTING STARS

Just three months after losing the Champions League final, Wenger was dealt a further blow when one of his key players left in acrimonious fashion.

Ashley Cole's long relationship with the club came to a bitter end in August 2006. The divorce was particularly messy, with the left-back making the short move to London rivals Chelsea.

Less than a year later, Thierry Henry was gone too. After an injury-hit 2006-07 season, the club's record scorer joined Barcelona, the team that had denied Henry and Wenger in the French capital.

Both Cole and Henry went on to win the Champions League with their new clubs too.

AN OLD TRAFFORD NIGHTMARE

Manchester United 8 (yes, eight) Arsenal 2.  At a ground where the Gunners had clinched the title in 2002, Wenger suffered one of his greatest football humiliations in August 2011.

With his team shorn of several first-team regulars due to injuries and suspensions, the Arsenal manager watched on as his patched-up side were torn to shreds by their long-time rivals.

Rooney led the way with a hat-trick and Ashley Young scored twice, while Danny Welbeck, Nani and Park Ji-sung also found the net, as Arsenal suffered their worst defeat since 1896.

To rub salt in the wound, Robin van Persie missed a first-half penalty against the club he would later join, while full-back Carl Jenkinson was shown a red card in the second half.

CITY SLICKERS INFLICT WEMBLEY WOE

Wenger has enjoyed plenty of success at Wembley, lifting the FA Cup at the famous stadium on several occasions, including the 2017 showpiece when Arsenal denied Chelsea from completing the double.

However, the League Cup has not been so kind for the former Grampus Eight boss.

Having lost the 2007 final against Chelsea in Cardiff, he suffered Wembley disappointment four years later when Obafemi Martins came off the bench to clinch unfancied Birmingham City the trophy at Arsenal's expense.

Yet this season's final loss to Manchester City was perhaps even tougher to stomach. While Pep Guardiola clinched his first trophy with the Citizens in style with a resounding 3-0 triumph, Wenger once again faced questions over his Arsenal future after failing to secure the one domestic honour that eluded him.