The 2019–20 season sees Olimpia Milano competing in both EuroLeague and Lega Basket Serie A. The first is the highest level of European basketball competitions, for which Milano has a license. While in the Italian Serie A, Milano needs a confirmation after having lost the previous year championship in the semifinal against Dinamo Sassari, despite being the favourite team.
 For the second year in a row, Olimpia Milano is sponsored by Armani Exchange.
 The 2019/2020 is a season of big changes and unfortunate epilogue due to the COVID-19 pandemic.
 After having lost in any competitions of the disappointing 2018-19 season, the team first replaces the president Livio Proli with Pantaleo Dell'Orco and then the head Coach Simone Pianigiani. Ettore Messina is called to manage the team for the 2019/2020 season
 Messina stated during the press conference of his presentation that the season objectives are to win the Italian Serie A and to reach the EuroLeague playoffs.
 The season had a great start in Euroleague with seven wins and only two losses, while in the Italian league Milano struggles to find continuity. Soon the team starts vacillating also in Euroleague where, after the successful run, they manage to lose nine games out of twelve.
 Milano ends the first half of the season with a disappointing loss in the derby against Cantù, when Messina expressed his concern about the ongoing season. The management was compelled to some corrective actions by releasing Aaron White and Shelvin Mack, after their unsatisfying performances, and hire Keifer Sykes (who joined the team already in December) and Drew Crawford, the latter only for the Euroleague.
 The 2020 was the year of the coronavirus pandemic outbreak that interested first Italy and then spread out all over Europe. The Lega Basket was the first organization that decided to suspend the competition to both comply to the government directives and avoid spreading the virus amongst the players. Meanwhile Real Madrid announced on 12 March that one player was positive to the virus, only six days after the match against Milan. Euroleague followed with the decision of interrupting the competition while Milan decided to voluntarily enter in quarantine.
 During the pandemic period, Lombardy was the region in Italy which suffered the most from the coronavirus. The team and the players decided to devolve part of their salary to the region's health care.
 On 7 April the FIP, Italian Basketball Federation, declares the end of the season without winners.
 The same choice followed for the Euroleague season on 25 May and that concludes Milano's 2019-20 season.
 Supplier: Armani / Sponsor: Armani Exchange
 Due to the dramatic events connected to Kobe Bryant, Milano decided to honour him by using in the opening game of the Italian Cup a purple and yellow jersey. The second jersey with a predominant yellow colour and purple sides, was never used.
 Note: Flags indicate national team eligibility at FIBA-sanctioned events. Players may hold other non-FIBA nationality not displayed.
 6+6 format (colours: Italian or homegrown players; foreign players; young players; injured players)
 Drew Crawford was hired in January, after the injuries in the small forward role of Moraschini and Brooks. His Euroleague escape was used for the transfer. Crawford could be used, though, only in the Euroleague because there was no room left for more foreign players in the roster for the Italian championship, the last spot was taken by Keifer Sykes.
 The following players have been called from the youth team and have made their appearance in the championship.
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 The following players have joined the team for the preseason matches. Biligha, Brooks and Della Valle where playing in the Italian national team for the World Cup. In the same competition Roll was playing for the Tunisian team. Gudaitis and Nedović were out because of physical condition.
 Aleksandr Šaškov is under contract with Milano and last year played on loan for V.L. Pesaro.
 In the current season the team organization introduces a new element in the Italian Basketball where the head coach covers both the role of coach and president.
  
 Source: Competitions
 The 2019–20 LBA season is made of 17 teams, which means that a team will skip two rounds during the season. Milano will not play in round 15 and round 32.
 Source: Competitive matches
 Due to the COVID-19 pandemic in Italy the Serie A games could not be scheduled regularly. An emergency government decree was issued in the night of 7 March, which put at risk the regular prosecution of the competition A following decree established that all the competitions and players gathering had to be suspended until 3 April.
 After the Italian Basketball Federation (FIP) meeting, the season came to an early end without winners, the following matches were cancelled.
 Source: Competitive matches
 On 12 March Euroleague decided to suspend the championship after the COVID-19 pandemic all over Europe and some European teams were as well affected. Despite the various attempts to restore the season  the executive board decided to definitely cancel the season and the following games were never played.
 Milano qualified to the 2020 Italian Basketball Cup having ended the first half of the season in 2nd place. They lost the semifinal against Reyer Venezia.