Friendlies, Coppa Italia, Serie A: Milan prepare for the true start of 2025/26 season

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The month of August is the winding down of the summer and, in turn, the start of the new season. For AC Milan, there is a lot to get ready for. 

It has been a long summer, even if it does not feel like too long ago that Milan were recovering from that Coppa Italia final defeat. Time has flown, but the pain of last season remains there, present and ready to reappear.

For this reason, the Rossoneri have to start the season positively. There is no credit in the bank; last season did not do that. Of course, there may be a little more generosity, but there will be no one who is happy or even content with a poor start.

Season sliproad

Things continue this weekend, where Milan will face Leeds United at the Aviva Stadium in Dublin, and then make the trip to Stamford Bridge to face Chelsea. Making it four Premier League opponents this summer.

It is also entirely possible that these games may be slightly harder than the tests against Liverpool and Arsenal, solely due to the games being closer to the start of the season. However, we will find out this weekend.

Nevertheless, it will be interesting to see how Massimiliano Allegri handles these two fixtures. After all, two games in 26 hours is a little ridiculous, especially when you have to take rest, recovery and travel into the mix.

Coppa Italia

It has been 22 years since the Diavolo last lifted the Coppa Italia, and if they are to do so again this year, it will require A LOT. Milan will not be granted an easy path, given they come in to the tournament in the early stages.

Last season, the club entered the tournament in the Round of 16 at the start of December. Despite reaching the final, that same luxury will not be awarded to them. There is no trophy to show for that, and there is no easier run for it either.

coppa italia trophyPhotos: Francesco Scaccianoce + Marco Rosi/Getty Images

Instead, the Rossoneri will enter the tournament in the first round and will face Bari at San Siro just a week after the game against Chelsea (August 17th). Of course, this asks a lot of the team mentally. However, it will probably be a chance for Allegri to test his reserves and rotation players.

Last season, Napoli were taken to penalties by Modena, before eventually being knocked out of the competition by Lazio in the Round of 16. In other words, not having Europe does not make the season easier in this regard.

Season begins

Then, we have the true beginning of the season. The first two games of Serie A, which fall on Saturday the 23rd and Friday the 29th. Cremonese at San Siro and then Lecce at Stadio Via del Mare. Two, on paper, relatively easy starters for Allegri.

However, we all know how this can go.

Last season, Parma proved to be a much more difficult opponent than imagined, and the Rossoneri started, pretty much, as they meant to go on. That cannot be repeated this season; again, they do not have such a luxury to do so.

At the start of August, the time of writing this, the pre-season has been a relative success. The mercato only needs visiting a few more times and the team already looks to have an Allegrian personality.

Milan players before Liverpool gamePhoto by AC Milan

That all goes out of the window on Matchday 1, though. Only then can we see the credentials of the summer’s work. A big month awaits Milan, indeed.

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