Santiago Gimenez’s selection dilemma: Will Massimiliano Allegri trust him to start Milan’s Coppa Italia game against Bari?

The first official whistle of the new season is upon Milan, and with it comes an unusual reality. Instead of easing into their campaign through Serie A, the Rossoneri are forced to begin with the Coppa Italia preliminary round, a stark reminder of the price they paid for their underwhelming eighth-place finish last season. At the San Siro, Bari awaits — a club Milan hasn’t faced in over 14 years, since their last Serie A encounter in March 2011.

The question that lingers, however, is not only whether the Rossoneri players can assert their dominance early but also one of intrigue: Will Santiago Gimenez start in this crucial tie?

The 2025-26 season kicks off under Massimiliano Allegri’s second reign at the club, and the coach has already stressed the importance of restoring the club’s prestige. A Coppa Italia preliminary round is far from glamorous, yet it serves as a timely warning.

This clash, therefore, is not just a hurdle but a statement. The message is clear: Allegri’s players must win, both to advance and to prove their ambitions are back on track. Should they succeed, Lecce awaits in the next round at the end of September, where a spot in the last 16 will be at stake.

Allegri’s formation dilemma

For Allegri, though, the issue is not so much about Bari’s threat as it is about balancing his squad. The pre-season offered some positives, but the tactical direction for the campaign remains under debate.

According to Il Corriere dello Sport, the 58-year-old is still evaluating formations, oscillating between a 4-3-3 and a 3-5-2 setup. His final choice will dictate how Milan approaches the contest — either with width and pace or with a tighter midfield control.

The attack: Leao, Pulisic… and the Gimenez question

What seems certain is that Rafael Leao will feature prominently. Alongside him, Christian Pulisic, who was recently a doubt due to an ankle knock, looks set to start. That leaves the question everyone is asking: what about Santiago Gimenez?

The Mexican striker, one of Milan’s headline January additions, is expected to be on the bench. While his arrival has raised expectations, Allegri appears to favor starting with a familiar attacking duo before unleashing Gimenez if needed, reports Gazzetta dello Sport. This suggests that for now, Gimenez’s role will be that of an impact substitute, a player to shift the dynamic should the contest remain in the balance.