Arsene Wenger’s Euro woe and his last shot at redemption
While Arsene Wengers first match as Arsenal manager is officially listed as a 2-0 win against Blackburn at Ewood Park on 12 October 1996, it is almost forgotten that the Frenchman effectively took charge two games earlier.
During half-time of a Uefa Cup fixture at Borussia Moenchengladbach, an impatient Wenger left his seat alongside David Dein in the stands and entered the away dressing room to issue tactical instructions to a team that, it had recently been confirmed to the bemusement of English football, this scholarly figure would soon be formally inheriting.
His gambit failed – the Gunners, trailing 4-3 on aggregate at the interval, ultimately lost 6-4 – yet although it did not hint at the glorious transformation that Wenger would soon oversee, that result was in some ways a fitting note on which to begin a 22-year tenure that remains, even with the end now in sight, conspicuously bereft of a European trophy.
Wengers European drought truly is remarkable for a multitude of reasons: the sheer number of continental campaigns he has helmed; how unfavourably his record compares to his domestic achievements and, more damningly, the records of the other managers to whom he is often compared; and how many times opportunity has seemingly knocked – only for it to be spurned.
For a man adept enough at knockout tournaments to boast more FA Cups than all but three English clubs, it is curious that he has never managed to repeat the trick in Europe over the course of two decades.
That absence of silverware looks even more glaring alongside the achievements of his contemporaries: Sir Alex Ferguson and Jose Mourinho have four major European titles, Carlo Ancelotti and Rafael Benitez three, and Pep Guardiola two.
A litany of anticlimaxes
His greatest disappointment came in the 2006 Champions League final, where Arsenal led a Barcelona side featuring Ronaldinho and Samuel Etoo until the 76th minute, despite the early dismissal of goalkeeper Jens Lehmann, only to lose 2-1.
He would never come closer to the biggest prize of all, and Wenger has cited it as the worst moment of his reign.
Chelsea ended Arsenal's European hopes in 2004, despite the Gunners going unbeaten in the league (Source: Getty)
The 22 years contain a litany of other Champions League anticlimaxes, though.
Losing to Chelsea in the 2004 quarter-finals deprived the Invincibles of a realistic shot at the top prize in a year when the European giants fell by the wayside and Jose Mourinhos Porto went on to steal the show.
Other missed opportunities came in 2008, when Arsenal fell to Liverpool in a see-saw quarter-final that swung on two late goals, and a year later when they reached the semi-finals but were well beaten in the second leg by Manchester United.
In the early days Wengers team struggled to replicate their title-winning Premier League form on the European stage, losing to the likes of PAOK Salonika, Dynamo Kiev and Lens and falling at the first hurdle in his first three full seasons.
Even when, in the last of those, Champions League group stage elimination parachuted Arsenal into the Uefa Cup and they reached the final, they contrived to lose on penalties to a Galatasaray team who finished with 10 men.
Arsenal lost on penalties to Galatasaray in the 2000 Uefa Cup final (Source: Getty)
Wengers later Champions League campaigns, meanwhile, became characterised by repeated and increasingly demoralising drubbings at the hands of Bayern Munich and Barcelona.
Monaco near misses
Wenger already had scars from European competition before arriving in north London, however.
In 1990, his third season in charge at Monaco, they reached the semi-finals of the Cup Winners Cup, where they lost to a great Sampdoria team, spearheaded by Gianluca Vialli, who would go on to claim the title.
Werder Bremen beat Wenger's Monaco in the 1992 Cup Winners' Cup final (Source: Getty)
Two years later, they made the final and were fancied to beat Werder Bremen but, without star player George Weah and emotionally affected by a stadium disaster that had left 18 French fans dead and thousands more injured just a day earlier, they lost 2-0.
In 1994 he steered them to the semi-finals of the nascent Champions League, but again they lost to the eventual winners, in this case an AC Milan side which crushed Johan Cruyffs Barcelona 4-0 in the final.
It has not all been heartbreak and misery in Europe, though.
Some of Wengers finest moments at Arsenal have come in the Champions League: the 5-1 sacking of Inter Milan at the San Siro in 2003, an improbable victory at star-studded Real Madrid on the way to the 2006 final, a giddy if ultimately futile first-leg win over Pep Guardiolas all-conquering Barcelona team in 2011.
Winning 5-1 at Inter Milan was one of Wenger's finest hours at Arsenal (Source: Getty)
But no trophy, despite his obvious yearning for one, and now just one chance to do so before he is ushered out of N5.
The stakes for Thursday's Europa League semi-final with Atletico Madrid, then, are high: Wenger arguably needs European silverware more than he ever has, since the likelihood of him enjoying a glorious send-off rest solely on winning the tournament.
Revisiting his record in these competitions, and the formidable recent history of Atletico, offer scant encouragement.
But it would be a delicious irony for the 68-year-old if he were to answer that criticism in the season when his detractors have finally got their way.