Diego Flaccadori (born 5 April 1996) is an Italian professional basketball player for Olimpia Milano of the Italian Lega Basket Serie A (LBA) and the EuroLeague. He stands 195 cm (6’4¾") tall, and he can play at both the point guard and shooting guard positions.
Flaccadori came through the youth ranks of Excelsior Pallacanestro Bergamo, before transferring to Basket Treviglio, where he made his debut for the club's men's team in the amateur Italian third division during the 2013–14 campaign. He played 26 games in his first year in men's basketball, averaging 2.5 points a contest.
Flaccadori then joined Dolomiti Energia Trento of the professional Italian top-flight level league Serie A in August 2014. In his first season with the team, he saw the court in 34 games in the Italian League, scoring 2.8 points per outing. In the 2015–16 season, he marked his debut on the European club stage, participating in the European 2nd tier Eurocup competition with Trento.
He was an early entry candidate for the 2016 NBA draft, but later removed his name from the list.
On 31 July 2019 Flaccadori signed a two-year contract with Bayern Munich of the German Basketball Bundesliga (BBL) and the EuroLeague.
On 20 July 2021 Flaccadori returned to his former team Aquila Trento on a one-year loan.
Flaccadori was part of the Italian junior national teams on several occasions. He competed in the 2012 FIBA Europe Under-16 Championship, guided the Italian Under-18 national team to gold at the 2014 Albert Schweitzer Tournament, he was picked by the website Eurobasket.com for their unofficial 2014 FIBA Europe Under-18 Championship's Second Team the same year, was named to Eurobasket.com's unofficial 2015 FIBA Under-19 World Championship All-Second Team, and also played at the 2015 FIBA Europe Under-20 Championship.