Arsene Wenger has experienced every emotion possible during his 20 years in charge of Arsenal, from guiding the Gunners' 'Invincibles' to the league title in 2004 to seeing his side crucified in midweek by Bayern Munich in the Champions League.
The Frenchman has helped the north Londoners to add three Premier League titles, six FA Cups and six Community Shields to their trophy cabinet during his two decades in charge. But despite his success, the uncertainty over his future is bigger than ever.
Indeed, it's been almost 13 years since the league title last arrived at the Emirates, during the days of Thierry Henry, Martin Keown, Dennis Bergkamp and Patrick Vieira. And while the league title and success in Europe has eluded Wenger since, the 67-year-old has picked up some painful and rather humiliating defeats along the way.
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Perhaps it's no coincidence that Arsenal have largely struggled for silverware in the years since their incredible 'Invincibles' season, and the following seven worst moments of Wenger's reign as Gunners boss may help to explain why.
While one of, if not the most, respected managers in the Premier League after how he’s changed English football, Wenger’s future was thrown into doubt on several occasions during a number of testing times for the club.
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Tottenham 5-1 Arsenal - January 2008
The only consolation for Wenger's team on that memorable day for Spurs fans in 2008 was that the humiliation occurred at White Hart Lane, rather at the Emirates.
So embarrassing were the Gunners that William Gallas had to act as the peacemaker when Nicklas Bendtner and Emmanuel Adebayor nearly broke out in a fight, mid-match.
Defeat may have been in the League Cup rather than the league, but it didn't ease the pain of their heavy loss ending a nine-year run where Spurs had failed to beat their north London rivals, before going on to beat Chelsea 2-1 in the final.
Arsenal 1-2 Birmingham - February 2011
For any manager who is just one victory away from ending a six-year wait for a trophy against a team they are odds on to beat, it's no surprise Wenger dropped to his knees when a disastrous piece of defending cost Arsenal the League Cup.
A defensive mix-up between Wojciech Szczęsny and Laurent Koscielny allowed Birmingham loan star Obafemi Martins to pounce and secure Birmingham a late victory just as the game appeared to be going to extra time.
In the end, while the Gunners finished fourth in the Premier League, the Blues were relegated and have yet to return to England's top flight.
Manchester United 8-2 Arsenal - August 2011
Red Devils fans will never allow Arsenal to live this down, as United humiliated Wenger's side so early in the season - which resulted in the Frenchman's future being thrown into doubt.
Arsenal were still adapting to life without Cesc Fabregas and Samir Nasri, who left for Barcelona and Manchester City respectively, and Wenger responded by signing Mikel Arteta, Per Mertesacker and Andre Santos on transfer deadline day.
But Gunners fans will feel they acted too late, as they were dismantled without two of their key players, while Carl Jenkinson was given a second-half red card to compound Wenger's misery.
Manchester City 6-3 Arsenal - December 2013
Wenger may have looked back on his side's defeat at the Etihad as the defining moment in the 2013/14 title race.
The Gunners were top of the table going into their game at City, before being thrashed by a Manuel Pellegrini side that had to fend for themselves in the second half without star striker Sergio Aguero, due to injury.
Indeed, some offside claims and a penalty call were dismissed in favour of Arsenal, but City's attack was just too much for Wenger's men to cope with, eventually finishing the season in fourth - seven points off Pellegrini's eventual title winners.
Liverpool 5-1 Arsenal - February 2014
In typical Arsenal fashion, second half of the season syndrome kicked in and Wenger watched on from the sidelines as his then-top of the table side were tortured by the Reds in a disastrous first half.
By the 10th minute, Martin Skrtel had netted twice, while Raheem Sterling and Daniel Sturridge sent Arsenal into half-time stunned. And Sterling found the net again in the second-half, while Mikel Arteta's penalty was no consolation.
The Gunners were two points clear of Manchester City and Chelsea in February, but come the end of the season they were languishing in fourth.
Chelsea 6-0 Arsenal - March 2014
It was not simply the scoreline that made it a humiliating afternoon for Wenger, but the fact that the Frenchman's 1000th game in charge of Arsenal saw defeat inflicted by their local rivals.
Wenger's rival Jose Mourinho was also in charge on that day, as the Gunners suffered their heaviest defeat to the Blues in 107 years of competitive meetings between the two sides.
For the first time during his time in charge of Arsenal, Wenger failed to attend his post-match press conference, as he saw his winless run against the Portuguese boss extend to 11 matches.
Bayern Munich 5-1 Arsenal - February 2017
Wenger's future as Arsenal manager may be partially dependent on this one result, as the north Londoners were swept aside by the Bavarian giants with relative ease.
Having been beaten by the Bundesliga outfit by the same scoreline just 15 months earlier, it would have been expected that the Frenchman had learned his lesson from the previous Champions League tie.
However, Wenger did nothing to ease the pressure on himself as his side face a seventh consecutive last-16 exit from the competition.
Arsenal's failures in Europe are a concern amongst the fans, and their recent defeat to the Bavarians helped to fuel supporters' desire for Wenger to leave.