Three Positions That Milan Must Bolster This January

Following an impressive start to the season, Milan’s weaknesses began to surface during the last couple of months. Although the brilliant work conducted by club directors Paolo Maldini and Ricky Massara can’t be questioned, Stefano Pioli’s squad remains far from being a finished article. So despite a busy summer, the Rossoneri could once again resort to the transfer market to fill some of the holes within the team and boost their chance in upsetting their crosstown rivals in the Scudetto race. So let’s take a look at the three playing positions that Milan must bolster this January.

Center Back

Some say that one can rarely sign a top quality player in January, but let’s not forget that Milan landed a wonderful center back last winter.

Of course we’re talking about Fikayo Tomori, who has been one of the best defenders in Serie A thus far this season.

Nevertheless, the former Chelsea man needs backup, especially following Simon Kjaer’s injury setback.

Alessio Romagnoli is slowly regaining his best form, but the captain’s future remains uncertain due to his expiring contract, while Matteo Gabbia is yet to prove that he’s up to the task,

Therefore, the Diavolo could use a new center back, and Lille’s Sven Botman appears to be the primary target.

However, the Dutchman’s hefty price tag could prove to be an issue for Milan, which is why Francesco Acerbi might be a decent alternative.

The Italian’s first experience at the club was a forgettable one, but that was a long time ago. A section of the Lazio Utlras want the Euro 2020 out of the capital, so it remains to be seen if he’ll be placed on market.

Finally, the club might consider recalling Mattia Caldara from his loan spell, but one would imagine that Venezia wouldn’t like the idea of losing a key defender in the middle of the campaign.

Central Midfielder 

Since the start of the campaign, Franck Kessié and (to a lesser degree) Ismael Bennacer have been unable to replicate their impressive displays from last season.

And yet, their absence (due to the African Cup of Nations) will leave a major gap in the middle of the park.

Sandro Tonali has been the star of the show in midfield, but Tiemoué Bakayoko hasn’t impressed at all since his return to Milan.

And even if the Frenchman takes his game up a notch, Milan will have little to no depth in central midfield between January and early February, which could cost them dearly – especially if Inter manage to widen the gap at the top of the table.

Unfortunately for Maldini, there are very few convincing and at the same time realistic options on the market. A report claimed that Tottenham outcast Tanguy Ndombele has been proposed.

Sassuolo’s Filip Djuricic has been mentioned as well, but the Serbian might be more fitting for the attacking midfielder role.

The management will be awaiting new opportunities to arisen.


Even though Milan need some fresh blood upfront, their pursuit of a new striker will probably have to wait until the summer, as a new winger could a more urgent priority for January (Rade Krunic serving as a left winger tells the whole story).

On the right wing, Alexis Saelemaekers continues to blow hot and cold, while Samuel Castillejo’s struggles continue.

On the opposite flank, Rafael Leao and Ante Rebic are both solid options, but they can often be found on the treatment table or even covering upfront.

Therefore, a new versatile winger would be a welcomed addition, and Hakim Ziyech could turn out to be the latest Chelsea wantaway who enjoys a career revival at Milan.

The Moroccan international possesses some stunning magic within his feet, and his qualities would surely please the San Siro crowds.