Way, way back, at the start of Arsène Wenger’s first full season with Arsenal, a side that would win the Premier League and FA Cup double come the end of the campaign, endured a moment of the purest European misery. It was inflicted by underestimated Greek opponents. In the opening round of the Uefa Cup, Paok Salonika were the visitors to Highbury. An Arsenal team containing the talent of David Seaman, Tony Adams, Patrick Vieira, Emmanuel Petit, Marc Overmars, Dennis Bergkamp and Ian Wright dominated, and were searching for the goal to win the tie when Paok’s Zisis Vryzas scythed through them three minutes from the end to deliver a classic sucker punch.

The home crowd, the players who knew they should have done better and an anguished Wenger experienced that jab of desperate deflation. Some 18 years on from that Paok punishment, the exact same sensation arrived as Arsenal spun from the elation of Alexis Sánchez’s header to the burning frustration of Alfred Finnbogason’s flicked match-winner for Olympiakos. For Wenger, that sudden sinking feeling, like leaving your stomach behind as a plane suddenly drops in mid-air, assailed him yet again. This was not supposed to happen. Every time it seems to hit Arsenal like a shock, and yet it happens often enough that it should not be remotely surprising.

Over his 18 years of consecutive Champions League football, Wenger has presided over 177 games in the competition. That is a big old number. As you might imagine, there has been a wide spectrum of performances and experiences within that. Some outstanding (beating Real Madrid in the Bernabéu with a Thierry Henry special), some routine (a straightforward 2-0 home win over Standard Liège for example) and some hideous (last season’s calamitous 3-1 defeat by Monaco sums up this batch quite well).

The trouble with making the same type of mistakes repetitively over 18 years and 177 games is that it becomes unacceptable that Arsenal seem unable to learn. To change. To adapt. To try to do things differently. With that much experience of Champions League football, and with – on the whole – pretty good players for this level at their disposal, it reveals a very deep-rooted problem to know all about the banana skin in front of you and still go flying. That 177 is an admirable number in a way, reflecting consistency few others match in terms of Champions League qualification, but in another way it is damning. All those games. Same old naivety.

Arsenal’s difficulty in controlling games, this tendency for anxious football that makes them chase and put all their emotion into trying to force a situation before they fall apart, has become an unwanted hallmark in Europe. Any opponents who are well organised, committed, and try their luck have a chance of profiting if Wenger’s team slip into this self-destructive mode. This season Dinamo Zagreb and Olympiakos have done it. In their past three home games in the Champions League Arsenal have resorted to this brand of hectic, disorganised football and on each occasion shipped three goals, to Anderlecht, Monaco and Olympiakos. These are not the clubs from the Bayern Munich, Barcelona and Juventus stratosphere but teams Arsenal were comfortable favourites to beat at home.

From a headline perspective, Wenger left himself open to criticism with the Petr Cech/David Ospina situation. His ambiguous explanation over the selection of the second (and weaker) choice, with the semi-disguised hint of an injury worry over Cech, was unhelpful. If Cech had a clear injury concern then picking Ospina was reasonable. If not, it begs the obvious question as to why a manager would not pick his only purchase of the summer in a key position for a must-win game.

But beyond that debate, the broader question boils down to why Arsenal play with this strung-out recklessness in the Champions League. Why they find it so hard to be calm. Wright called it “schoolboy” stuff, but surely they should know how to better control games of this nature by now. It is only when the causes are more or less lost, in the knockouts once they have blown the first leg, that they can relax and put in a heroic (but not quite good enough) winning performance.

Vieira said something revealing about Wenger’s management style in the documentary he made with Roy Keane a while ago. The manager’s biggest strength? “Trust,” said Vieira. “He will trust his players. He will try to make you make the right decision by yourself. Not him telling you what he expects or what he wants you to do … that can be a weakness as well.”

Wenger does trust his players to work out problems on the pitch for themselves, but perhaps this causes some of the anxiety when a game becomes complicated. Maybe the players need some more exact instruction on how to handle an unpredictable match, as the Olympiakos contest turned out to be. To concede goals straight after working their way back into the game was as much in the mind as in the technique.

The years of unbroken qualification from the group stage are a badge of honour for Wenger. He may pull it off this season again, unlikely though it seems, because Champions League football can be bizarre like that. The Arsenal manager will remember the 2003-04 campaign, when his team had only one point from their first three games and went on, strangely enough, to win their group.

Even if they can summon a similar near-miracle this season, Wenger’s holy grail of winning the Champions League one day remains improbably distant.