I Rossoneri have endured a difficult few seasons, and it is almost ten years since they last won the Serie A title. The golden days where the likes of Kaka, Shevchenko and Ronaldinho were turning out at San Siro is a distant memory, and a major rebuilding operation is now underway.
Manager Stefano Pioli is trying to resurrect a team with a limited budget; owing to severe financial difficulties, leading to their exclusion from this season's Europa League for breaking financial fair play regulations.
But looking upward, the side has some seriously talented young players making waves and drawing attention from Europe's top clubs. They have also showed an element of smartness in recent transfers, ensuring they don't overspend again.
The return of club icon Zlatan Ibrahimovic has added experience this campaign, but further reinforcements will surely be needed to propel Milan back to where they belong, in the upper echelons of European football. Here's what they might (eventually) look like at the start of next season.
GK: Gianluigi Donnarumma
The youngest ever Italian international goalkeeper, who made his Milan debut at 16, is now in his fifth season as the undisputed number one at San Siro.
Although the giant shot-stopper is one of the most sought-after keepers in world football, he will continue his development in Milan for the time being and the team will be more than happy with that.
RB: Andrea Conti
A late developer who only secured a regular spot in the Milan side this season, Conti has beaten off competition from young Davide Calabria over the course of the campaign.
The pacy full-back, who loves to get forward, will be looking to rediscover the form that earned him the move to San Siro from Atalanta in 2017.
CB: Alessio Romagnoli
The ball-playing centre-half took over as club captain last season after the return of Leonardo Bonucci to Juventus, and has stepped up to the challenge with maturity beyond his years.
Romagnoli is destined for great things for both club and country, and will be the player the side look toward for inspiration as they look to challenge for European football again next season.
CB: Kristoffer Ajer
Heavily linked with Milan earlier this month, young Norwegian defender Ajer has been turning out excellent performances for Celtic and is in high demand across Europe.
He would make an excellent partner for Romagnoli with his strong tackling ability and tenacity, and if Milan can fight off the competition with an offer of first team football, he'd be a steal at almost any price.
LB: Theo Hernandez
A real bright spark for Milan this season, Theo Hernandez has been a revelation on the left flank for Pioli's side after signing from Real Madrid last summer and looks set to become a fan favourite if he sticks around.
Club legend Paolo Maldini is said to have coerced the Frenchman to join by flying to Hernandez's residence in Ibiza in person. That's commitment.
CM: Ismaël Bennacer
The former Gunner (who never actually played for Arsenal) has had an excellent breakthrough season after his move from Empoli.
The diminutive Algerian midfielder – who can sit deep as playmaker or further forward in the mezzala role – has formed an ever improving partnership with Franck Kessie this season and will be looking to push on when football returns.
CM: Franck Kessié
Bennacer's midfield partner; 23-year-old Franck Kessié is (somewhat ironically) a transfer target for Arsenal this summer, but it is thought Milan will be able to hold on to the highly-rated Ivorian.
The strong central midfielder is an excellent dribbler and is often the instigator of many of the side's attacking moves and counter attacks. Will be key to his team's development in the next phase of the rebuilding job.
RW: Mario Gotze
World Cup final goalscorer Matio Götze has just had it publicly confirmed that he will be departing Borussia Dortmund this summer when his contract expires, leaving him out there for any club who think they can squeeze some quality out of him.
Milan could use his experience, speed and European knowledge to great effect, and he could slot in to Milan's system in a variety of ways. It wouldn't be a surprise to see the German at San Siro next season.
LW: Hakan Çalhanoglu
Turkish star Çalhanoglu has been ever-present on the left side for Milan since his move from Bayer Leverkusen in 2017.
The skilful set piece specialist faces competition from Lucas Paquetá for his place in the long term, but looks still very much part of the blueprint for I Rossoneri in the years to come.
ST: Ante Rebic
Rebic moved to San Siro from Eintracht Frankfurt as part of a two year loan swap deal with Andre Silva last summer, and so far things have worked out pretty well for the Croatian.
Seven goals in 18 games represents a strong return considering he is often deployed as a second striker or an attacking midfielder behind Ibrahimovic, and Milan fans will be hoping he can kick on next season and seal a permanent move.
ST: Luka Jovic
Jovic has recently also been linked with a two year loan deal to San Siro, and it's easy to see why. The Serbian has suffered a difficult first season at Real Madrid and has struggled to get off the bench at the Bernabeu.
If Milan were to secure his services (and if his success in Frankfurt wasn't a fluke) he would add goals to the team, and he would get the chance to kickstart his career. Everyone's a winner.