The season restarts for Milan next weekend with the Coppa Italia before our first Serie A game back takes place on June 22, and it promises to be an important two months.
While it looks unlikely, we have a 12-point deficit to make up in the battle for a Champions League qualification spot, albeit Atalanta also have a game in hand.
Further, with a number of key figures missing for our Coppa Italia semi-final second-leg clash with Juventus next Friday, the odds are stacked against us in Turin as we try to keep our hopes of winning some silverware this season alive.
In turn, there is a lot on the line still collectively, and similarly, there is plenty at stake on an individual level for certain players too.
The core of the side is arguably set. Gianluigi Donnarumma, Alessio Romagnoli, Theo Hernandez, Ismael Bennacer, Hakan Calhanoglu and Zlatan Ibrahimovic are likely to be named in our starting XI if available and fit.
Beyond them, there is another group of players who have proven their importance to the side and will perhaps remain with the likes of Samu Castillejo and Ante Rebic proving their worth.
However, question marks arguably hang over some of the others and over the course of the next two months, they could essentially be playing for their futures at Milan, or at the very least, their place in the starting XI.
The 23-year-old has made 17 appearances so far this season, as he has struggled to cement his place in the side while injury and suspensions have been problematic too.
After making his breakthrough in the 2014/15 campaign, it appeared as though he had a bright future ahead of him. Unfortunately, through inconsistency and lapses in concentration which have led to some glaring mistakes, he has looked increasingly vulnerable over the last two seasons.
In turn, if he can’t establish himself as the first-choice at right-back over the course of June and July, or at the very least as a competent back-up option, it could become a concern for him.
Similarly to Calabria, Conti has also struggled to establish himself as a reliable and consistent figure at right-back. He’s made 18 appearances so far this season, and he’s still struggling to get back to the form he displayed at Atalanta.
The 26-year-old has been through a lot after back-to-back serious injuries and perhaps they have taken their toll on him, but if he wants to be our first-choice option in that department, he has to improve still.
As noted by Il Milanista, PSV Eindhoven ace Denzel Dumfries is said to be on our radar, and so if neither Conti nor Calabria can prove their worth, they could find themselves out of the side next season, or worst yet, possibly out of the club.
With his current contract expiring in 2021, Milan have a decision to make. They could either extend his deal or look to offload him this summer to avoid losing him for nothing when he becomes a free agent.
As noted by Football Italia, his agent recently insisted that he wants to stay. However, is that the smart move for the Rossoneri?
With Matteo Gabbia coming through and a potentially cheaper back-up option in stalwart Simon Kjaer, coupled with Leo Duarte trying to make his comeback from injury, could it mean an exit for Musacchio? He’ll hope to prove his importance as a better option than those names if given a chance to do so in the remaining games.
If there is one area of the current Milan squad which has been talked about a lot, it’s the midfield. Bennacer is surely now one of the first names on the team-sheet given how important he has become for us, but it’s about finding the best option next to him.
Kessie offers tenacity, combativeness, work-rate and mobility in midfield, but he has continued to let himself down by not taking his game to the next level, specifically in terms of his offensive play and impact in the final third, as seen with tallies of just 13 goals and nine assists in 121 games.
The 23-year-old arguably has all the attributes needed to be a dominant figure in midfield for us going both ways, but he has continued to fall short. If that continues in the next couple of months, he could see a new face arrive to push him down the pecking order as with Lucas Biglia and Giacomo Bonaventura set to leave when their respective contracts expire, reinforcements will be needed to fill those voids.
Despite arriving to much fanfare in January last year, it hasn’t worked out as hoped for the Brazilian ace thus far.
He’s managed just one goal and three assists in 36 appearances for Milan, and for a player of his quality and the expectation that came with his arrival, that’s simply not good enough.
Sooner rather than later, he’s going to have to start to show us something to suggest that he warrants a stay and more opportunities, otherwise he may well find himself facing real question marks hanging over his future with us as there will surely be better options out there if he can’t produce.
Similarly to Paqueta, the facts and figures don’t lie. The 20-year-old has managed just two goals and two assists in 22 appearances so far this season.
That’s not the type of return expected of him despite still being so young, and while his pace, movement and threat to the opposition defence can all be lauded, he needs to be more decisive.
While it remains to be seen what happens with Zlatan Ibrahimovic after he sustained an injury in training last week, that puts the pressure on Leao to potentially lead the line in his absence. If he can prove he is capable, keeping Ibrahimovic and starting Leao could be the way forward next season.
If he can’t, then perhaps a decision might need to be taken over a player who reportedly cost €35m last summer, as per Football Italia. With just 26 goals in 28 league games so far this season, our blunt attack needs addressing and if Leao continues to struggle, it could result in changes being made to give us a more prolific presence up top.
Perhaps that’s harsh considering it’s his first year with us, but he must still perform at a high level regardless to show that he can produce when the level of pressure and expectation goes up.