The Biggest Milan Derby For 20 Years Is Coming

And there we have it, mark May 10 and 18 down in the diary.

Inter’s 5-3 aggregate win over Benfica means that for the first time in 18 years there will be a Milan derby Champions League tie once again; a full two decades since the last Derby della Madonnina Champions League semi final.

The two best teams left in the competition might be on the other side of the draw, but the drama, the tension and the atmosphere belongs solely to the Milan pair.

These games won’t be as high in quality as the Real Madrid-Manchester City legs, yet the stakes will be higher, the need to make it into the final that much more precious. Not just for prestige reasons, but for monetary ones.

As it stands, Milan are sitting fourth in the Serie A and will make it back into the Champions League next season. Inter, having a true Jekyll and Hyde season in which they can see off Barcelona, Porto and Benfica but lose to Monza, Empoli and Bologna, are sitting fifth.

Inter has made around €82m ($89m) from their run to the semi final in UEFA
EFA
prize money (excluding match day revenue from Champions League nights), but with club debt still at eye-watering levels of €350m ($383m), making the competition is imperative for the future of the club.

Milan have earned €85m ($92m) from their run to a first semi final appearance since lifting the trophy in 2007. Yet the difference between the two is that Milan’s finances are in much better shape than their cousin’s, with Milan posting losses of €66m ($72m) for 2021/22 (which could be theoretically wiped clean with the incoming UEFA prize money).

On a purely finance level, Milan could probably live without Champions League football next season. Inter, by contrast, need to be in the competition, and at this stage, the only way to do that is by winning it.

The situation becomes even murkier as the shadow of Juventus looms large over both. As of writing, it looks more than likely that Juve’s 15 points deduction will be overturned, and thus the natural order of the table being restored.

Should that happen Juve, in one stroke, would jump to third in the table, pushing Roma down to fourth. Suddenly, both Milan sides are out of the Champions League places, making the semi final even more important, the tension becoming even more heightened, unbearable even to some. Suddenly, there’s more than just city bragging rights at stake, but potential glory and in Inter’s case, avoiding financial meltdown.

Yet what chances do either of the Milan two have of actually winning the trophy? On the surface of things, Inter would likely be a better representative of Serie A in the final than Milan. Both have been remarkably inconsistent this season, at times outdoing each other in the ‘who can follow up a great result with a bad one’ stakes, but in a one-off game in a final, the general feeling is that Inter could potentially get the job done against Madrid or City more than Milan.

Inter, by and large, have the better players and have morphed into a great cup side under Simone Inzaghi, himself a player more accustomed to sparkling in cup games than the lengthy rigours of the league season.

There’s also some apprehension that both Milan sides could get embarrassed by either Madrid or City on the grandest stage. Both struggle against teams with pace and both Madrid and City simply possess better players across the pitch than either of the Milan duo. Napoli, now out, would’ve been Italy’s best bet to win the competition in that respect.

Yet for now, Istanbul is something far off in the distance for supporters of Inter and Milan. All that will matter is May 10 and 18, when the biggest Milan derby for 20 years will bring the city to a complete standstill.

And there’ll be much more than civic pride on the line.