Now, after two decades at Arsenal, 15 trophies, a new stadium and almost £700m spent on players, he is the longest-serving – and most successful – overseas manager this country has known.
But what will Wenger’s legacy be? To some, he is responsible for transforming the English game. To others, his initial success petered out and he will be judged on a run of 12 years without a league title.
Here, we analyse his record and examine the myths – is he really a reluctant spender and was his second decade really a let down? – of a tenure that began in a different era, his first match coming in a pre-internet age:
The ‘top-four trophy’ and the actual trophies
Wenger was heavily criticised in 2012 when, with the club contemplating a seventh season without silverware, he suggested finishing in the top four – and therefore qualifying for the Champions League – was effectively a trophy in its own right.
“The first trophy is to finish in the top four,” Wenger said following an FA Cup fifth-round exit at Sunderland. “I believe finishing fourth is vital for us, so let’s focus on that.”
If that were indeed the case, his tenure would have been an unequivocal success, having guided Arsenal to a top-four finish in every one of his 20 seasons in charge.
Have his second 10 years been a let-down?
Wenger’s introduction of new training techniques and a different approach to nutrition helped sustain and advance the careers of many of the players he inherited, including the likes of then-captain Tony Adams, keeper David Seaman and striker Dennis Bergkamp.
Those players formed the spine of a team that won the double in Wenger’s second season, the first of three league titles for Arsenal in eight years, culminating in the remarkable success of the Invincibles in 2003-04.
That season, the Gunners went the whole campaign unbeaten, ultimately setting a new record of 49 games without defeat in the top flight.
But there has been no league title since and, after the FA Cup triumph of 2004-05, Arsenal endured a run of nine years without a trophy, a sequence ended by the 2013-14 FA Cup win and followed by a further success in the competition the next year, as well as two Community Shields.
So is it right to say Arsenal have performed significantly worse in the second half of his reign?
Their record is actually remarkably similar in that period to the first decade under Wenger.
Is he too loyal to his players?
Ensuring Arsenal’s successful evolution beyond the 1998 double-winning team and the Invincibles was never going to be an easy task.
One accusation levelled at Wenger is that he is not ruthless enough and is too loyal to players in whose development he has invested time and energy.
Earlier this year, Martin Keown said: “He treats every player like his own son. When Francis Coquelin was brilliant last season, Wenger should have gone another step higher and said ‘no, let’s go and get a world-class central midfield player’.
“That would put fear into the rest of Europe, but he’s very loyal, almost too loyal.”
While it is hard to judge exactly when a player is past his best, it is certainly the case that Wenger’s Arsenal are more likely than any other leading club to keep players for longer.
Source: BBC SPORTS