You have to go back a couple of years to find Milan in a similar predicament as this week, but on second thought it somehow looks worse this time.
Then, with the Champions League final approaching and the Scudetto already gone Juventus' way, Milan coach Carlo Ancelotti was anxious to show he could indeed win the Big One.
His determination to achieve his goal was even bigger because Juve, his former club where a shameful section of fans had resorted to vilifying him at every turn, were the opponents in the Old Trafford final.
You could then forgive Ancelotti's exuberant reaction when Andriy Shevchenko sent Gianluigi Buffon the wrong way on the game's last penalty kick, after regulation time and extra time had barely produced a shot at goal from either side.
Once he had kicked that huge monkey off his shoulder, Ancelotti set upon the task of winning his first Scudetto, which he did last year when Juve's ambitions collapsed under the vulnerability of their defence and Roma could only finish second.
Milan being Milan, with their huge following, high expectations and other kinds of pressure - being the Prime Minister's own team can bring rewards but also add an element of discomfort when you know you cannot put a foot wrong - their main goal this year was always going to be a second Champions League trophy in three years.
To their credit Ancelotti and president Adriano Galliani - who in his other capacity as League president will have the odd privilege of handing the newly-rediscovered Serie A trophy to Juve next Sunday - have always insisted that winning in Europe would have meant more to them this year than, er, simply adding another Scudetto.
Whether this was to take pressure off Milan's season-long chase of Juventus is arguable, but the smokescreen dissipated two weeks ago when Juve, playing their typically disciplined, headstrong game, won at the San Siro 1-0 and all but bagged the League title.
Milan paid lip service to their determination not to give up - after all, it had taken them less than eight days in mid-season to rally from an eight-point deficit - but the general feeling was they'd now turn their attention to the task of beating Liverpool in Istanbul.
Their last two Serie A matches ended in draws, 2-2 in Lecce and 3-3 at home to Palermo on Friday night, which created an almost unheard of event in Italian football, as Juventus were crowned as champions without even playing on the day. It had apparently happened only once before, in 1905.
Against Palermo, Ancelotti fielded what amounted to a reserve side, although some of the names in it (Rui Costa, Serginho, Tomasson, Crespo) would have you think otherwise.
But this in fact does nothing but reinforce the notion that Milan had a stronger overall squad than Juventus and should have performed better. And you get the feeling Ancelotti feels the same when he says he wouldn't swap his team with any other in the world.
Whether he will still feel the same after the final in Istanbul is open to debate, of course.
Seriously, Milan have taken an ultra-cautious approach to the match against Liverpool by resting all the probable starters agains Palermo. With a couple of days to go before kick-off the side seems set, the only slight was doubt about the identity of Shevchenko's partner up front: Inzaghi or Crespo?
Inzaghi has been regaining form after a long injury lay-off, while Crespo played on Friday and staked his claim for a starting place. Ancelotti has now confirmed it will be the Chelsea loan man who will start the match.
Barring a huge surprise, Ancelotti will play the customary 4-3-1-2 formation with Cafu, Nesta, Stam and Maldini in defence, Gattuso and Seedorf supporting Pirlo in midfield and Kaka filling the hole behind Shevchenko and Crespo.
As Milan followers will know, many believe the Rossoneri's fortunes depend on Pirlo's precise passing, and his form of late had been a concern.
When Milan played Juventus two weeks ago, Pirlo had barely got back into the side after missing a few matches because of injury but he looked out of sorts that day and he was rested against Lecce and Palermo.
His ability to position his body at the right angle for the short, one-touch passing he frequently he excels in, to his side's benefit, adds another dimension to Milan's midfield, as much as Kaka's running with the ball and Cafu's overlapping on the right, but he'd looked tired recently and Ancelotti's decision to rest him for the last two outings will surely have helped.
As those who saw Milan suffer in the semi-final return leg in Eindhoven will know, the side seemed to have lost some of their brilliance and Pirlo was but one of those who appeared spent.
You'd be surprised, for example, at the criticism the San Siro faithful have been directing at Seedorf in the last couple of months. The Dutch midfielder had been a solid performer but a lack of precise passing and a passive outlook have put him in the fans' doghouse.
The defence has been another sore point: generally thought of as one of the best around, it has proved to be vulnerable to high balls, and Paolo Maldini, for all his wonderful class, cannot be left completely alone on the flank as he was in Eindhoven.
Even Dida, who has made some unbelievable saves this season - isn't that a sign that things in front of him aren't so great? - has slipped a bit recently, and it all adds to a slight feeling of anxiousness.
That was brought to the surface by Milan's team doctor, and director of the much publicised Milan Lab medical centre, Jean Pierre Meersseman, who said: 'I am more worried than I was before the final two years ago.'
Let's not get this wrong: on their day, and their day has come frequently in the last few years, Milan can beat anybody and put on a show while doing it, but their performances in the last 30 days and a loss of form for a couple of key players means fans, more so than the side itself which has rarely shown signs of worry, feel a slight sense of trepidation on the eve of the Istanbul match.
With 48 hours to go the ticket allocation had not been entirely sold, in part because Istanbul is an expensive trip (the ultras have managed to keep prices down to €400 for their day trip, average prices for a same-day return journey are €600 including tickets for the top tier of the stadium).
So Milan will not be spurred on by the sea of red-and-black clad legions that, for example, made the 1989 final in Barcelona against Steaua Bucarest an unforgettable event, with an estimated 70,000 Milan fans in the stands.
This will make Milan's task just a little bit harder, but, as former Houston Rockets coach Rudy Tomjanovich once said to doubters, never underestimate the heart of a champion.
Milan surely belong to that category, with a huge amount of talent thrown in, but they must show it one more time on Wednesday, tired legs or not.
From
Soccernet
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