As season openers go, Milan have had easier than an away trip to PSV Eindhoven's Philips Stadion in a crucial Champions League qualifier.
The Dutch side came into the encounter with five competitive games under their belts—all of which they won. Any preseason doubts about how they'd fair without top-scorer Dries Mertens, now of Napoli, and with Phillip Cocu on the bench were quickly dispelled.
But then, scoring 16 goals and conceding only three in the space of a handful of games will do that.
Milan had history with PSV and the Philips Stadion, too.
In 2005, the Rossoneri lost there, but they progressed thanks to a win at home, and in 2006 they were bested by the Dutch side in the group phase of the competition.
Milan fans have cause to feel their side got the short straw in the draw as well.
Of all the games in the play-off round for this year's UCL, this is the only tie to feature two former European champions. The 1988 champions, PSV also have a great home record against Italian sides in European competition, W7 D1 L3.
The Eredivisie runners-up haven't featured in the Champions League group stages since 2009, but they have pedigree, including 12 appearances between 1997 and 2008.
In that context, coming away with a 1-1 draw might be seen as a positive.
Stephan El Shaarawy's early header means that Milan have the away-goal advantage, even though they'll be disappointed to have drawn the game thanks to Tim Matavž's exploitation of a Christian Abbiati error.
PSV were the more impressive side on the night against Milan, even with El Shaarawy's goal. The home side had twice as many shots on target, and were missing star-man Zakaria Bakkali, a 17-year-old who's scored four goals already this season. Assuming he's fit, they'll be a better side in Milan and more dangerous for having learned from their mistakes in the first leg.
Speaking to the club's website after the game, Cocu said:
We were happy to show this is the football we want to play. We dominated the game from the first whistle. We put AC Milan´s defence under pressure and created goalscoring opportunities. We will obviously analyse the match and continue our learning process. We must see to it that we will not make the same mistakes in the next match.
Milan have a slender advantage, but they can't afford to be complacent.
PSV hammered Napoli 3-0 in Eindhoven and then won 3-1 in Naples in last season's Europa League. And if they can overcome Napoli at the Stadio San Paolo, Milan's San Siro will hold little fear for them.
The goals against Napoli came from Maertens, Jeremain Lens and Marcelo—all of which have now moved on. But in Italy, all three strikes belonged to the aforementioned Matavž, the young Slovenian striker needing just 30 minutes to bag his hat-trick.
Against Milan's sometimes-questionable back line, he'll be a constant threat.
Cocu's side is built around energy, youth and attacking football. Not only do they have the youngest squad in the whole competition, but the former Barcelona midfielder has already started a game this season using a starting XI with an average age of under 20 and no-one over the age of 22. A good example of their attacking prowess can be seen in their 5-0 drubbing of NEC Nijmegen.
In a lot of ways, it's a model that Milan have been trying to emulate. Since Silvio Berlusconi vowed to tighten the purse strings at Milanello a couple of seasons ago, the focus has been on youth development and long-term planning.
With PSV, the benefits of such an approach are easy to see. They've sold Mertens to Napoli, the influential midfielder Kevin Strootman to Roma, and Mark van Bommel' has retired. Yet they still look solid.
Even with bringing in the odd veteran like Ji-Sung Park, the average age of this summer's signings is just 22. They players who left averaged 27. They've also made upwards of €23 million on the transfers.
It's the sort of club you'd like to see progress in European competition and reap the rewards of its positive, sensible approach to the business of football. With an estimated €30 million up for grabs from qualification, it's the kind of pay back club directors dream of.
Unless you're at a major side like Milan, that is. Then, the qualification process becomes more a nightmare than a dream. The Champions League is not something the Rossoneri aspire to—it's something they need.
The seven-times winners not only see elite European competition as the least to be expected of a club of their stature, the tournament now has a financial imperative.
Milan are desperate not only to balance the books, but also to invest money into the squad, something that will be nigh on impossible without the big cheque from UEFA.
From a footballing standpoint, losing out to the Dutch would have disastrous consequences for Milan and for Max Allegri. Berlusconi isn't the coach's biggest fan, and though the pair now have something of an entente cordiale, there are few who believe the peace would withstand failure to qualify.
Progression will get Allegri's side off to the right start. Failure will almost surely result in the manager losing his job and the side being thrown into turmoil. A new manager will be hard to find and he'll have little to spend.
It should be too early to even think this, but Milan's season hangs in the balance.