AC Milan’s preparations for their return to Serie A action have taken another frustrating turn, with Rafael Leao ruled out once again and new signing Christopher Nkunku not yet fit to start.
The Rossoneri face Bologna at San Siro on September 14, but Massimiliano Allegri will be without his most explosive forward and unable to fully unleash his £36 million arrival from Chelsea. For a team already under pressure after an uneven start to the season, the timing could hardly be worse.
Leao setback forces Milan to rethink
Leao has not featured since limping off with a calf problem during the Coppa Italia tie against Bari. The expectation was that the international break would give him enough time to recover, but medical staff are reluctant to take risks. According to Calciomercato, the Portuguese forward trained separately from the squad this week, a sign that his progress remains slower than hoped.
Milan now see the Udinese clash in the following round as a more realistic target for his return. It is a cautious approach, but one rooted in hard lessons from last season, when Leao was rushed back too soon from a hamstring injury and struggled to regain full sharpness.
The absence of the 26-year-old is no small issue. Leao has been Milan’s most decisive attacking player in recent years, scoring 37 goals and providing 31 assists across all competitions since 2021. His ability to carry the ball at pace, isolate defenders and turn tight games with a single run makes him irreplaceable in Allegri’s system.
Nkunku still waiting for his moment
If Leao’s absence is frustrating, the wait for Nkunku is at least tinged with anticipation. Signed for £36m from Chelsea, the Frenchman is seen as a marquee addition to help restore Milan’s presence in the Champions League spots.
Nkunku has trained well since joining but is not deemed ready to start. Instead, Allegri may use him from the bench against Bologna, offering supporters their first glimpse of a player who scored 58 goals in 88 Bundesliga games for RB Leipzig before his move to England.
Milan’s medical and fitness staff are determined to manage his introduction carefully. Nkunku endured a disrupted campaign at Chelsea with recurring injuries, and Allegri has stressed the importance of “building his rhythm gradually.” That measured approach reflects both the player’s recent past and the club’s long-term investment.
Allegri’s tactical dilemma
The absence of Leao and limited availability of Nkunku leaves Allegri short of attacking options. The likely frontline against Bologna will feature Christian Pulisic and Santiago Gimenez.
Pulisic, who returned from international duty with the United States earlier this week, has been one of the few bright sparks this season. His sharp movement and link-up play offer structure in the final third, but without Leao stretching defenses, Pulisic risks being isolated.
Gimenez, meanwhile, carries momentum after scoring for Mexico in a friendly against South Korea. Milan signed him in the summer to add goals after finishing eighth last season, and Allegri will hope the 24-year-old can provide presence in the box against Bologna’s well-drilled back line.
Bologna test comes at a difficult time
Bologna are not an easy opponent for Milan to face while short-handed. They stunned the Rossoneri in May by beating them in the Coppa Italia final, a result that still lingers in the minds of fans and players alike. Their organized defensive structure and counter-attacking threat pose the exact type of challenge Milan have struggled with when missing key attackers.
Allegri’s side have also been inconsistent in the early stages of the season. A shock 2-1 defeat to Cremonese on opening day exposed lingering vulnerabilities from last year, though a 2-0 win over Lecce briefly steadied the ship.
The coach has made clear that restoring discipline and balance is his first priority, but without Leao and Nkunku at full tilt, finding goals will remain a pressing concern.
A club searching for stability
Milan’s struggles have been magnified by their recent decline. Last season’s eighth-place finish meant no European football for the first time in a decade (excluding the 2019-20 Financial Fair Play ban). For a club of Milan’s stature, that absence is a painful reminder of how far they have fallen from their 2000s peak.
Leao’s decision to stay this summer, despite strong interest from Bayern Munich and Barcelona, was a statement of loyalty and ambition. Milan need him fit and firing if they are to return to Europe. Nkunku’s signing was supposed to ease the burden, but his adaptation will take time.
In the meantime, Allegri must rely on pragmatism, defensive organization, and opportunism in attack. That formula might be enough to see off Bologna, but the bigger question is whether Milan can compete over a full campaign without risking more false starts.
For now, the focus is on managing short-term difficulties while keeping an eye on the bigger picture. Getting Leao back without setbacks is priority number one. Integrating Nkunku into Serie A gradually is a close second.
