Two possible systems, one key player: How Christian Pulisic could solve Massimiliano Allegri’s Milan dilemma ahead of Coppa Italia

As Milan prepares to launch its new season, Massimiliano Allegri finds himself at a tactical crossroads. The Rossoneri have completed their pre-season schedule, but the coach is yet to decide which system will best serve the team moving forward. Two main options remain on the table — a balanced 4-3-3 or a more structured 3-5-2 — and, intriguingly, Christian Pulisic could be the key to solving this dilemma.

The upcoming match against Bari, on paper, should be straightforward for Milan. Yet Allegri knows cup ties can produce surprises. “San Siro will be expecting a performance,” wrote Gazzetta dello Sport, noting that the coach is working through his final preparations at Milanello with athletic drills and short games, but no fixed tactical setup just yet.

Throughout the summer, the experienced Italian boss rotated between different systems. In the Asian tour and in matches against Leeds and Chelsea, he used a fluid, chameleonic 3-5-2 (or 3-5-1-1) far more often than the 4-3-3 that had seemed his original plan.

That original 4-3-3 was meant to provide a sturdier defensive shield compared to the more attacking 4-2-3-1 of previous seasons, offering extra midfield presence to protect the back line. Allegri had been clear in his unveiling press conference: “To return to fighting for the top of the table, the first thing to do is concede fewer goals.”

Still, the 3-5-2 has offered its own advantages: defensive stability, wing-back width, and tactical versatility. It also maximizes the depth in midfield, where options such as Ruben Loftus-Cheek, Youssouf Fofana, and Samuele Ricci can be rotated.

Squad options for Coppa Italia clash

For the Bari match, Mike Maignan will start in goal, with Fikayo Tomori, Matteo Gabbia, and Strahinja Pavlovic forming the defensive trio. Gazzetta dello Sport suggests that the 3-5-2 will be Allegri’s choice this weekend. On the flanks, Alexis Saelemaekers and Pervis Estupinan are expected to provide width, while the midfield trio will likely feature Loftus-Cheek, Ricci, and Fofana.

Up front, Rafael Leao will once again link with Christian Pulisic, though the American may operate in a slightly deeper role — a subtle shift that could influence the entire tactical equation.

Pulisic’s role in the tactical puzzle

This is where Allegri’s dilemma deepens. In a 4-3-3, slotting Pulisic into the left or right forward role is straightforward. But in a 3-5-2, the picture becomes more complex.

As Gazzetta dello Sport notes, “While positioning Pulisic in a 4-3-3 is easy… in this 3-5-2 it becomes a bit more complicated.” The issue is that placing him behind the strikers in a 3-5-1-1 or 3-4-1-2 removes a midfield spot, forcing Allegri to choose between multiple strong central players — Loftus-Cheek, Fofana, Ricci, Modric, Jashari, and possibly Musah.

Yet the American’s recent form and impact make him hard to ignore. Described as one of the Rossoneri’s most consistent performers over the last two seasons, he has shown the ability to roam centrally and create, something both Paulo Fonseca and Stefano Pioli briefly tested in the past.