One prominent London newspaper's back page headline was "Arsene Who?" -- a jibe at the Frenchman's apparent lack of credentials when it came to his less than stellar playing career or the fact that he had no experience of English football.
Fast forward two decades later and Wenger has signed a new two-year deal, but the response from many Arsenal fans might be "Arsene Why?"
After all, the Gunners' fifth place in the English Premier League this season resulted in the club failing to qualify for the Champions League for the first time since 1997.
Adding insult to injury, their great rivals Tottenham finished above them, which hasn't happened since 1995, a feeling Wenger had been hitherto unaccustomed to experiencing.
In a statement, the club's majority owner Stan Kroenke said Wednesday that Wenger was the "best person" to fulfill the club's ambitions of winning the Premier League and other major European trophies.
Wenger himself said he was "looking forward to the future with optimism and excitement" after committing his future to the club.
"We're committed to mounting a sustained league challenge and that will be our focus this summer and next season," said Wenger in a statement.
The Frenchman and Kroenke reportedly met on Monday to determine the 67-year-old's future, with the decision relayed to directors at a Tuesday board meeting.
By Wednesday, the longest-running soap opera in English football was set to enter its 22nd season, and who can possibly say if the plot twists have come to an end.
In his 21 years with the club, Wenger has transformed Arsenal both on and off the field, overseeing the move from their iconic Highbury Stadium to their plush new home down the road at The Emirates.
He inherited a squad with a mentality of grinding out wins -- not for nothing was the chant "One nil to the Arse-nal" associated with them -- and while the Gunners were undoubtedly a force within English football, it was Wenger who turned them into a powerhouse.
His continental approach brought in innovative training and dietary techniques. And instead of an emphasis on British players, Wenger often favored foreign signings, paying relatively low amounts of money for young, raw talent.
The likes of Wenger's fellow Frenchmen Thierry Henry and Patrick Vieira brought a dynamic spine to the side and the results were staggering.
Within two years, Arsenal had won the domestic double -- the Premier League and FA Cup -- which was even more impressive considering they chased down Sir Alex Ferguson's Manchester United to win the league.
There was undoubted bad blood between Wenger and Ferguson -- and it sometimes manifested itself on the pitch between the players -- but ultimately there would be mutual respect between the managers.
And yet with one feud on the wane, Wenger then locked horns with then Chelsea boss Jose Mourinho, who made it personal at times, labeling the Frenchman a "specialist in failure."
The "failure" tag was almost impossible to justify, considering Wenger has won 16 trophies in English football, including a further two Premier League titles and seven FA Cups.
In what some thought could have been his final game in charge, the 2-1 victory over London rivals Chelsea last weekend -- a side who finished 18 points clear of Arsenal on their way to the league title -- meant that Wenger's seventh FA Cup triumph, and Arsenal's 13th, made both him and his team the most successful in the competition's history.
But surely his greatest achievement to date has been his "Invincibles" of 2003/04, who went the entire league season without losing a single match.
The 26 victories and 12 draws will go down in English football folklore, with the swashbuckling style of play a delight to watch, a fact Wenger was keen to emphasize, as he explained to CNN World Sport's Alex Thomas in 2011.
"I believe football is first entertainment," he said. "It becomes business when you have to pay people. But we did not create football because we wanted to create business.
"We created football because we wanted to have fun ... that's why I think it's dangerous always in our job to think its first business.
"No, its first fun, enjoyment, and happiness. And we hope people come to the game on Saturday's for enjoyment."
But ultimately, the holy grail for Wenger and his team -- an elusive Champions League -- has yet to be won. They reached the final in 2006, even taking the lead in Paris against Barcelona after goalkeeper Jens Lehmann was sent off.
But two late goals did for them. It remains the nearest they have got to lifting the trophy. And by 2017, Arsenal's departure in the round of 16 marked the seventh straight year they've exited the tournament at that stage.
Even more humiliating was that the 10-2 aggregate defeat against Bayern Munich, marking the largest ever loss for an English side in Europe.
Meanwhile, a fair number of Arsenal fans, who once believed that Wenger could do no wrong, had turned on him, demanding he walk away from the club, even resorting to the hiring of biplanes, brandishing banners pleading with him to leave (it should also be pointed out that pro-Wenger banners have also adorned the skies).
The factors were numerous for supporters wanting "Arsene Out." Aside from not winning the Champions League, the team haven't won the Premier League since 2004.
Little wonder that this section of the fan base believed that the club had turned into a selling club, rather than spending big on world-class players, although the likes of Alexis Sanchez and Mesut Ozil were prominent signings.
But with neither player yet to commit his future to the club, it remains to be seen whether Wenger remaining at the helm will still result in departures: just not his own.