The last time the Gunners won a piece of silverware – the 2005 FA Cup final – modern legends Robert Pires, Patrick Vieira and Dennis Begkamp were still in the side.
The match, which Arsenal played in a uncharacteristically defensive fashion, proved a watershed for the club.
Vieira departed the club after sealing the trophy, with new talisman Cesc Fabregas the fulcrum of the side. It was also the last season that the club displayed any pragmatism.
In the seasons following the triumph the new model for the direction for the club has been bold and idealistic. Arsene Wenger has relied almost entirely on the youth system to create attacking, beautiful football.
However, while the increasingly stylish play has won admirers it has not won trophies and, for the first time in his run in charge, Wenger might finally lose the fans.
The atmosphere at the Emirates last season, especially in the 1-0 reverse against Newcastle, was one of discontent and frustration. In the last few days, former players, including Tony Adams and Lee Dixon have been critical of Arsenal’s weaknesses.
So is it time for Arsenal to do the unthinkable? Or can Wenger turn the tide?
While Arsenal have not won a trophy for a while, they have become a regular Champions League side under the guidance of Wenger. They have never finished outside the top four under the Frenchman and have become one of the world’s most financially sound football clubs.
The team is a young, attacking side and are only a few decent players away from becoming a force to be reckoned with.
Wenger’s success was primarily build on the foundation of a solid defence and strength from set pieces inherited by the previous management of the club. His weakness lies in his inability to replace the famous back five and has struggled since.
There have also been an influx of poor defenders including Nelson Vivas, Igors Stepanovs and Philippe Senderos, while the jury is still out on Seb Squillaci and Laurent Koscielny.
While Sol Campbell and Thomas Vermaelen are notable exceptions Arsenal have been short of defensive quality since the retirement of Martin Keown and Tony Adams.