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The birth and the Borletti era (1930-1955)

The birth of Pallacanestro Olimpia Milano is traditionally dated 1936, year of the first Italian League Championship title. Actually it was founded 6 years earlier (in 1930) as "Dopolavoro Borletti" by Fratelli Borletti managers. Borletti team won 4 consecutive Italian League Championships from 1936 to 1939.

In 1947, Milan businessman Adolfo Bogoncelli merged Pallacanestro Como and Borletti to form a new society, commonly known as "Borolimpia". "Borletti" brand was the main sponsor of the team, becoming the first sponsor in the history of Italian sport.

In 1955, after 9 Italian League Championships, Borletti brand leaves Olimpia Milano jersey.

The Simmenthal era (1956-1973)

The team regularly won the Italian League Championship in the 1950s and the 1960s, with players including Gabriele Vianello, Sandro Riminucci, Gianfranco Pieri, and Bill Bradley. In 1966, Olimpia won its first FIBA European Champions Cup.

In the 1970s, three teams were fighting across Europe for supremacy: Olimpia Milano, Ignis Varese, and Real Madrid. Pallacanestro Varese and Olimpia Milano were arch-rivals, as the two cities are 25 miles (40 km) apart. While Milano was a frequent Italian League champion, they were unable to win again the prestigious FIBA European Champions Cup. Late in the 1970s, the quality of the club declined, but Olimpia Milano still managed to win a FIBA Cup Winners' Cup.

In 1973, Simmenthal brand leaves Olimpia jersey after 17 years and 10 Italian League Championships.

1974–2007

In the 1970s through the 1980s, the team acquired several notable players, including the Boselli twins (Franco and Dino), Mike Sylvester, Chas Menatti, Dino Meneghin, Mike D'Antoni, John Gianelli, Roberto Premier. Bob McAdoo, Joe Barry Carroll, Russ Schoene, Antoine Carr, and Mike Brown. American head coach Dan Peterson led the team back to prominence.

In the 1980s, the team was sold to the Gabetti family. After this, they qualified for nine Serie A championships finals, winning five, with the 1987 team winning the Serie A title, the 1986–87 FIBA European Champions Cup (won also in 1988: both finals were won against Maccabi Tel Aviv), the Italian Cup and the 1987 FIBA Club World Cup. This gave the club the coveted "Triple Crown" and the even rarer "Quadruple Crown".

Led by point guard Sasha Djordjević, the team won another FIBA Korać Cup in 1993. Bepi Stefanel purchased the team franchise in 1994, and signed-up notable European players like Dejan Bodiroga, Gregor Fučka, Sandro De Pol, and Nando Gentile. In 1996, the team won the Italian Cup and its 25th Italian National Championship, celebrating the 60th anniversary of the club.

Team management was inconsistent, as ownership groups from 1998 to 2004. Players of the team included Warren Kidd, Hugo Sconochini, Claudio Coldebella and Petar Naumoski. In 2005, owner Corbelli, which bought the club in 2002, from Sergio Tacchini, was flanked by Adriano Galliani (managing director of Italian Football club A.C. Milan), Massimo Moratti (President of rival club Internazionale), NBA star Kobe Bryant, and stylist Giorgio Armani, as sponsor with the Armani Jeans brand. After difficult years, led by coach Lino Lardo, Olimpia reached the national championship Finals, finally being beaten by Climamio Bologna.

On January 25, 2006, in the midst of a disappointing season in the EuroLeague and domestically, Djordjevic was named as the team's new coach. He left as coach after the 2006–07 season, but not before securing Olimpia a berth in the 2007–08 Euroleague.

2008–present

In 2008, Giorgio Armani bought the team from Giorgio Corbelli, standing as the only owner, entirely changing the management structure, naming Livio Proli as president, and Lucio Zanca as general manager. Piero Bucchi was chosen to coach the new team, leading Olimpia twice to second place in LEGA Basket, being defeated by Montepaschi Siena in both cases.

In January 2011, after 23 years away from coaching, Dan Peterson came back from retirement at the request of team owner Giorgio Armani to replace Piero Bucchi, who was fired in mid-season. Peterson was hired on an interim basis and agreed to coach only the remainder of the season, in which he guided the team to the semi-finals. On June 9, Olimpia Milano announced Sergio Scariolo as new head coach for the 2011–12 season. The first player signed for the 2011–12 season was Omar Cook, an American-born play maker, who had played the previous season with Power Electronics Valencia. Owing to the NBA lockout, Danilo Gallinari went back to his alma mater, playing 15 games (8 in the Italian League, 7 in EuroLeague): he left the team in December. Sergio Scariolo was replaced by Luca Banchi at the beginning of the 2013–14 season, and the team brought from Montepaschi Siena: David Moss, Kristjan Kangur, and Daniel Hackett.

The team reached the quarterfinals of EuroLeague, 16 years after its last appearance, but the team lost against the eventual league champions, Maccabi Tel Aviv. The team finished in the 1st position the LEGA Basket regular season, and in the 7th game of the playoff's finals, Olimpia won its 26th Italian League championship title, its first after 18 years. Alessandro Gentile, the captain of Olimpia, was named MVP of the finals.

On June 29, 2017, Simone Pianigiani was hired as the new head coach and on June 15, 2018, Milano went to win his 28th title by beating Dolomiti Energia Trento in game 6 of the 2018 LBA Finals.

On June 11, 2019, legend Ettore Messina signed a deal as the new head coach of the club and president of all basketball operations for the following three seasons.

On May 4, 2021, the club reached the Euroleague Final Four after 29 years (1992 Final Four).