Arsène Wenger should really have consigned to history the brilliant victory scored in San Siro back when Cesc Fabregas was still the young presiding genius.
So much has happened since then – but sadly not much of it at Arsenal. Not, anyway, as far as competing seriously with a Milan side who seemed as though they were about to fall from the vine through sheer old age in 2008.
The reigning champions of Italy, and leaders of Serie A, still have some notable ancients about the place, as we saw when Clarence Seedorf, four times European champion, had a brief amble before returning to the bench, where he joined the illustrious Alessandro Nesta. But soon enough a terrible reality returned to any consideration of the strength of Arsenal's rehabilitation since the implosion of last season and the catastrophic start to this one. It was that, under coach Massimiliano Allegri, Milan have moved on. Arsenal have not – at least to any significant degree.
Not only did Wenger invoke the past, he produced it when he brought on Thierry Henry in the second half. The plan was for another romantic Last Hurrah before the great man returns to the obscurity of America's Major League Soccer, but the effect was forlorn as Milan drew huge dividends for their faith in the sometimes enigmatic superstars Zlatan Ibrahimovic and Robinho.
More than anything, Milan looked like a team who had been surely redirected towards some of the best of their past. They had an easy, biting rhythm, so coherent at times that Arsenal seemed to be playing a different game.
They were a team who looked without a touch of self-belief – and certainly one utterly unconvinced by their manager's talk of the imminence of fresh glory. The despairing reflection has to be framed in one question: if Wenger can't make Arsenal believe in themselves, who can?
Certainly, he has rarely talked the talk so eloquently, mystically even, as he did before the kick-off. He said Arsenal were close to perfection when Fabregas dethroned the reigning European champions in San Siro four years ago and they were building to the point where that superb triumph did not have to be anything more than a terrible reproach. With a shrug, he added: "If you meet a manager who is not an optimist he will not survive."
Unfortunately, Wenger's own chances of survival as a persuasive spinner of football dreams on football's biggest stage were put in early jeopardy by the superbly hit, 15th-minute goal of Kevin-Prince Boateng. It was the kind of goal guaranteed to undermine ambition more securely based than that created by Arsenal's brief surge of improved performance recently and, by the time Robinho added a second after 38 minutes, the idea of a renascent Arsenal was beginning to look like a fully fledged fantasy.
It didn't help that Wenger's decision not to start Alex Oxlade-Chamberlain apparently came from the belief that the patchwork flanks of the pitch would not only slow down Arsenal's latest boy wonder but also threaten injury.
As it happened, the build-up to Milan's first-half goals started wide, though in the case of the first one that is probably an extravagant description of Milan's contemptuous dismissal of what passed for Arsenal's defence. A poor clearance by Wojciech Szczesny was transferred to Boateng in the complete absence of close attention and his shot should have been the call to arms for a defence which was supposed to be on the point of healing itself. This process was badly affected by the injury which took Laurent Koscielny out of the game shortly before half-time, it is true, but by then this was a small detail in an unfolding disaster.
Not the least of it was the loss of authority by Thomas Vermaelen, who not so long was by some distance Arsenal's best chance of achieving acceptable levels of defensive security.
When he slipped in the face of another threat by Robinho, and saw the reanimated Brazilian slide the ball home quite beautifully for the third goal, it seemed less a mishap and more a statement about the hopelessness of Arsenal's cause.
Johan Djourou compounded Arsenal's fate when he allowed the knowing Ibrahimovic to persuade the referee to award a late penalty. The big man converted it for a final flourish in perhaps his most consistently impressive performance against English opposition.
His critical redemption in these parts was woven into the destruction of a team whose manager said that the good days were coming again. Not in Europe, certainly, and perhaps for some time only in their most optimistic dreams. Milan were extremely good at times, but there was no avoiding the fact that they were inhabiting another Arsenal nightmare.