For all Arsene Wenger's reputation as a continental football master, one of the anomalies of his career is that he's never quite mastered continental football. In fact, he's never won any of its competitions but been bridesmaid in all of them.
In 1992, his Monaco team lost the Cup Winners Cup final to Werder Bremen. In 2000, his Arsenal lost the Uefa Cup final to Galatasaray and, most recently in 2006, he saw the Champions League slip away against Barcelona.
The strong likelihood this season, of course, is that the wait will go on. Possibly indefinitely.
Indeed, such has been the scale of Arsenal's issues in this campaign that it almost seems preposterous to be talking about them as potential champions of Europe any time soon; particularly in the current context of the competition.
After a period in the mid-2000s when a series of teams who finished third, fourth and fifth in their domestic leagues illustrated how open and random cup football can be by lifting Europe's most prestigious trophy, the Champions League appears to have reclaimed its status as the continent's ultimate barometer of brilliance. In the last four years, all of its winners - Manchester United, Barcelona and Inter - have also claimed their domestic title in the same season. And, even more impressively, all of those victories were part of extended rallies of trophies.
That hardly gives hope to a team who haven't lifted any silverware in seven years and are desperately fighting to even qualify for the Champions League.
Worse, Arsenal's last two appearances illustrated just how far away they are from the competition's elite end as they were eliminated twice by Barcelona in relatively emphatic fashion.
As such, you would imagine Wenger has a little bit too much on his mind to be looking so far ahead. However, that would also involve discounting just how much the Champions League dominates his thinking.
Over the last two decades, much has been made of Alex Ferguson's "obsession" with the competition. But Wenger's is arguably equal to it and has never received anywhere near the same attention or examination.
Sources close to him testify that he sees it as a "gaping hole in his CV" and an objective more pressing than reclaiming the league title. He publicly hinted this himself a few years ago: "I want to win the Champions League but it's step by step. And to win not once but two or three times, to go into the history of European football."
Step by step is one thing though. One of the many idiosyncratic problems with Wenger's Arsenal is that they've never walked any kind of steady line in Europe. They've never shown the progression or learning curve that, say, Ferguson's Manchester United sides did between 1996-1999 or 2006-2008.
Indeed, perfectly illustrating Wenger's peculiar relationship with the competition, Arsenal have got to the final one season only to exit at the last 16 the next; or dismantled a European giant in one round before being eliminated by a smaller fish in the following.
His very first campaign arguably set the tone: in 1988-89, Monaco absolutely annihilated a very competent Club Brugge only to immediately fall to a mediocre Galatasaray.
And, if you do go back that far, his entire record is revealing. In a total of 15 completed seasons in the European Cup/Champions League, Wenger has reached the final once, the semi-finals twice, the quarter-finals and last 16 five times each and gone out at the first hurdle twice.
With Arsenal, his average round of elimination has been the last 16: exactly where he finds himself now. Hardly encouraging or edifying. And, for a style that seems so suited to European football, also hard to explain.
But then perhaps his Champions League record also reflects exactly why Wenger's career trophy cabinet isn't as glittering as it perhaps should be. Because, as his title-winning sides of 1998, 2002 and 2004 perfectly illustrated, Wenger's style of management and football both work best when his teams are at full confidence; when the new-age football comes off so naturally that they don't even have to think about it.
When that confidence is broken, however, it seems to take Wenger a long time to rebuild. And, not only might that explain why he's never retained a league title but also the oscillating European seasons. In short, his teams seem to find it difficult to overcome a poor domestic run to deliver continental results. The eliminations to Bayern Munich in 2005 and PSV Eindhoven in 2007 would appear perfect cases in point.
What's more, Wenger has never quite proven himself as tactically pragmatic in Europe as Ferguson or Rafa Benitez - England's last two champions. Both, for example, evolved and adapted. Wenger hasn't other than the run to the final in 2006; a run that was also built on Martin Keown's defensive work.
A lot will depend on his side's confidence. But that's also what now makes this tie with Milan so interesting.
Had Arsenal not won at Sunderland on Saturday then you could have been genuinely worried for them. Instead, they claimed the sort of late, electrifying victory against awkward opposition that can change mentalities and seasons. It may well prove their most significant result of the campaign.
But just as significant might be the exact make-up of this Champions League. In contrast to previous years, two of the best sides in Europe - Manchester City and Manchester United - are already out. Meanwhile, the continent's very best - Barcelona - seem to be struggling with complacency and conditioning. Should they meet Real Madrid early on, too, a path could well be cleared.
All of a sudden, we may end up with one of the most open Champions League seasons since 2007. It was around that period, of course, that Arsenal enjoyed their best ever performance in the competition.
And it seems it's going to take something similar if Wenger is ever to master that obsession.
• Miguel Delaney is a freelance European football writer and owner of Football Pantheon.