Milan vs. PSV Eindhoven Preview: All or Nothing

Things are never easy with Allegri’s Milan. First we chose the road less traveled by, which is why we are playing in the final qualifying round in the first place. Then we failed to put the game away last week in Eindhoven, which seemingly threw us into the fire. So now we have one last chance to qualify. Either a scoreless draw or a win. Allegri has left everything to chance, with all of our Champions League dreams on the line. It’s do or die, now or never, all or nothing. (Which clichés am I forgetting here?)

Allegri and Milan have left it all to the last minute... will we take fate by the horns, or let luck seal our fate?

Last week was not our finest hour. It is an epidemic with Allegri’s teams, from early on, he somehow fails to prepare the team, particularly mentally, to win from the first game of the season. Every team, every year it’s the same old story. And we knew when Milan also failed to secure the Champions League Group Stage last season that we were in danger of not qualifying still, even more so with the qualifying matches falling at the beginning of the season.

But I don’t know if Milan were prepared for the PSV side we met last week. Despite being embarrassingly young, even by the new Milan standards, they were incredibly driven, very dangerous on attack, and never gave up. Translation: they were hungry. Their inexperience showed at times, in fact a defensive slip up gave us the opportunity that we pounced on for our one goal. But it was also one of their many efforts and the follow-up that led to their equalizer. Translation: they are very dangerous.

Which Milan players will step up on Wednesday?

We should absolutely win on Wednesday. We have more talent, more experience, and we are playing at home. But we could absolutely lose, too. We start slow, we’ve been complacent way too often, and we make as many or more errors as their young team. In fact, I’m beginning to think that if the unthinkable happened, it wouldn’t even be an upset, even if it should be. Milan have just been less than convincing.

But Eindhoven are certainly not perfect. In fact, they drew 1-1 on Saturday to Heracles, their first slip-up in the league this season, where they had won their previous three matches. They also have a doubt for Wednesday, as their midfielder Wijnaldum was injured in that match. However, they may see the return of Bakkali, their 17 year old striker who is scoring goals and turning heads. (As if we didn’t already need to fear their attack enough already.)

Cocu knows Milan well, and there is no love lost

Cocu may have shown his cards last week, and hopefully Allegri will have some kind of answer to their game. But he has also seen our weaknesses, and will be incredibly determined to exploit them. And with good reason. Both he and a young Park Ji-Sung were part of the PSV squad that Milan defeated in the Champions League semifinals in 2005. To defeat Milan and prevent us from making the group stage would be the sweetest of victories, and give this young team a chance of a lifetime. So there is certainly no lack of motivation on their part.

I wish I could say the same for Milan. While the players should be motivated, so many are so young, they may not fully realize what is at stake. In three times that Milan have joined the group stage through the qualification route, they have always qualified. But can this squad dig deep and keep that tradition? Many have speculated that Allegri could finally be fired if he fails to qualify. With so much money on the line, it is possible. But after standing by him through last year and even re-confirming him, plus the lack of available options, I am not convinced. And I think Allegri knows this, too. So where there should be motivation, there may be a bit of complacency even from him.

If Boateng is part of the equation on Wednesday, will he be able to find solutions?

Boateng trained with the squad again yesterday and should be back, and De Jong was on the bench Saturday, so should be available. De Sciglio and Robinho are apparently fit again, too, so he actually has more options than last week. What will he do with this? He is notorious for not playing players who have been out injured for more than a week or two, so will he risk De Sciglio on either flank? We could certainly use him in a match like this. Will he put Boateng back where he belongs, in the midfield? Will he start Robinho, who was very dangerous in his few minutes on Saturday? He’s got a lot of experience that could be helpful. Or will he trust in youth for once, the players who have the same pace and hunger of the opposition? I typically believe in experience, but maybe youth is the answer to youth this time? Or maybe a healthy combination of both? I honestly have no answers to these questions, as Allegri is unpredictable enough in an average game, even more so when everything is on the line.

I don’t want to sugar coat anything. They are dangerous, we are not playing well, and one goal for them can seal our fate for this season. But on the flip side, Allegri has pulled performances out of this squad such as the one against Barcelona last year at the San Siro when Milan did the impossible. I said it before, I believe in this team. Even if it is hard to keep faith in Allegri, these players have something truly special. And I have to believe that when all of the chips are on the table, these guys are worth betting on. I never wanted to go the qualification route, and I had hoped that we could do better than the away goal advantage in the first round. But here we are, and despite all of my fears, I believe.

Our success cannot rest on the shoulders of just one player, especially one so young

I believe that we have a lot of talent available. And I believe in the red and black jerseys. I believe that when they put them on this Wednesday, some of the magic of the legends who have worn those shirts before will give them a little something extra. That glow from the seven Champions League trophies that were earned through the blood, sweat, and tears of previous generations of Milan – that glow will shine softly upon them and give them what they need to take this match, decisively, and see Milan through to where we should be: in the Champions League proper, into the group stages. Although it goes against all reason based on our season to date, I believe. I have to. I bleed red and black. And so do our heroes. Like all Milan players, they will leave it all on the pitch for the shirt. Because it’s all or nothing.

This post inspired by the music of The Cure’s “Faith” album

Our next match is

Champions League Qualification Round, 2nd Leg

AC Milan vs. PSV Eindhoven

Wednesday, August 28  20:45 CEST (2:45pm EDT)

This match will be shown on Fox Sports 1 in the U.S.

Check here for stream links before the match

Check out the latest Milan Obsession Podcast TOMORROW!