Wednesday, May 14, 2025

Coppa Italia Final • Milan vs. Bologna: One Cup to Rule Them All

Milan's season has been like a journey through Middle Earth, and we have found ourselves at the end of the season closer to midtable than where a club with this history belongs. We have battled Orcs, Trolls, and even a Balrog along our way. Perhaps our most amazing battle was defeating the Nazgûl in three of our five meetings, while drawing twice, including winning the Supercoppa at their expense and breaking the curse they held over us. But for a guaranteed place in European competition next season, we have one important battle left: the Coppa Italia Final on Wednesday. A win is the only acceptable outcome for our dignity, so the team have headed to Mount Doom to face Bologna for one cup to rule them all, and to Europe bind them.

The Fellowship of Milan are ready for the One Cup to rule them all...

Our Coppa Italia journey this season began with the Balrog of a manager who kept telling our best players, "You shall not play!" In December, in the Round of 16, we faced a familiar enemy, Sassuolo, but the Fellowship of Milan dismantled them 6-1. Under the leadership of a more Gandalf-style manager, in January, he oversaw the 3-1 Fall of Roma in the Quarterfinals. The Semifinals were the two-legged battle with the Witch King of Angmar and his Ringwraiths. In the first leg, we were evenly matched at 1-1, but in the second leg, we dominated those treble-bragging snakes with a 3-0 win and knocked them out of one competition, essentially taking another trophy from them (this time one they actually wanted.) However, it has been 22 years since winning this One Cup, so this final step of our journey is essential to lifting it once more for glory.

The battle for Midlle Earth... or at least the midfield... will be intense.

Our league status has been improving of late, including a 3-1 win on Friday over Bologna, our same adversaries on Wednesday. This was a huge improvement over when we initially faced them at the end of February and lost 2-1 away in a match that was controversially rescheduled due to flooding. While the Fellowship of Milan have been improving, Vincenzo Italiano's team have had some struggles with their form of late. Additionally, it has been 51 years since Bologna lifted the Coppa Italia, so their desperation could either produce a miracle or be their downfall.

On Friday, Italiano lined up a 4-2-3-1 with: Skorupski; De Silvestri, Beukema, Erlić, Lykogiannis; Moro, Freuler; Orsolini, Milan-owned Pobega, Domínguez; and Dallinga. He will be without Erlić, who was injured in our match, as well as Pedrola, who is also injured. However, he will have Holm, Ndoye, and Odgaard returning. Castro is struggling with a minor issue, so may not start, but will still be available. And of course, there will be our former captain, Calabria.

Our own Frodo and Samwise Gamgee will save the day.

Conceição has brought the entire Fellowship of Milan with him to Mount Doom... er... Rome... even the injured players. Sottil and Bondo are not expected to be available, but Conceição should have everyone else. In his press conference, the manager expressed doubts about Fofana, but it was reported that he trained in the final evening training with the team and should be available. Additionally, Leão will be available for this match. When asked directly whether he would be starting Jović or Santi Gimenez, he replied that even the players did not know this.

Just like the Fellowship faced trial after trial along their journey, the authorities in Rome have banned all coreografia, banners, flags, or pennants from the Milan section of the Stadio Olimpicao, while Bologna will still be allowed theirs. Milan's Curva Sud have been banned from these things all season due to the investigation and trial of the Ultras. But this is one match, it is away from home, and it is very unfair that one team is allowed to display their colors and the other is not. However, the Curva Sud has vowed to show up in full voice, which is louder than Bologna's Ultras anyway.

At the end of the day, we want to see the Fellowship celebrate like this.

The journey to get here has been long and fraught with perils. Some were self-inflicted, others were a result of the evil Eye of Cardinale. There were many heroes on the path to this cup, with 13 goals scored so far in thie tournament, including goals from Chukwueze, Reijnders, Leão, João Félix, Jović, and even a goal from a player who is now at Bologna, Calabria. Speaking of heroes, our wise Gandalf manager Conceição specializes in winning trophies, so I hope he brought his cigars and his boom box to Rome with all the players, because if Milan are triumphant, he will need them.

And while we all would have gladly chosen a different path and a different destination rather than relying solely on the One Cup, this is where our journey has taken us. Can this Fellowship of Milan, forged through the battles of Middle Earth this season, complete their task? Can they guarantee a place for themselves in the Europa League? And will we get to add the special Mark of the Coppa (patch) to our kits next year? We will find out at the final whistle on Wednesday. Then we will see who lifts the One Cup to rule them all.


This post inspired by the music of Marko Bosnjak's "Poison Cake"


Be sure to check out the latest Milan Obsession Podcast


Our next matches are:

Coppa Italia Final
Milan vs. Bologna
Wednesday, May 14, 2025 • 21:00 CEST (3pm EDT)
In the U.S., this match can be streamed on Paramount+,
or use a VPN to access better coverage




Campionato Primavera 1 Week 38
Milan Primavera vs. Genoa Primavera
Saturday, May 17, 2025 • 15:00 CEST (9:00am EDT)
This match is not being televised in the U.S.





Serie C Playouts
Milan Futuro vs. SPAL
Saturday, May 17, 2025 • 20:00 CEST (2:00pm EDT)
This match is not being televised in the U.S.




Serie A Week 37
Roma vs. Milan
Sunday, May 18, 2025 • 20:45 CEST (2:45pm EDT)
In the U.S., this match can be streamed on Paramount+,
or use a VPN to access better coverage