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On January 25, 2019, in a 100-94 loss to the Miami Heat, Osman scored a career-high 29 points. Four days later, Osman was named a participant for the 2019 Rising Stars Challenge as a member of the World Team after a stretch of notable career games.

On July 18, 2017, Osman signed with the Cleveland Cavaliers. On February 9, 2018, Osman played 38 minutes in a 123-107 Cavaliers victory over the Atlanta Hawks. He contributed 16 points on 6-of-9 shooting while notching 6 rebounds, 5 assists, and 3 steals. The Cavaliers made it to the 2018 NBA Finals, but lost 4-0 to the Golden State Warriors.

On June 25, 2015, Osman was selected with the 31st overall pick in the 2015 NBA draft, by the Minnesota Timberwolves. His draft rights, along with those of Rakeem Christmas and a future draft pick, were then traded to the Cleveland Cavaliers, in exchange for the draft rights to Tyus Jones that same night.

After playing with the junior national teams of Turkey, Osman became a member of the senior men's Turkish national basketball team. With Turkey's senior national team, he has played at the 2014 FIBA Basketball World Cup, EuroBasket 2015, and the 2016 Manila FIBA World Olympic Qualifying Tournament.

Osman was a member of the junior national teams of Turkey. He played at the following tournaments with Turkey's junior national teams: the 2011 FIBA Europe Under-16 Championship, the 2012 FIBA Europe Under-18 Championship, the 2012 Albert Schweitzer Tournament, where he won a bronze medal and was named the Most Talented Player, the 2013 FIBA Europe Under-18 Championship, where he won a gold medal, and at the 2014 FIBA Europe Under-20 Championship, where he also won a gold medal, and was named to the All-Tournament Team and selected as the MVP.

Osman signed a youth team contract with Anadolu Efes in 2007. He played for the junior, star, and youth teams of Efes. He was loaned for the 2011–12 season to the Turkish 2nd-tier level TB2L team, Pertevniyal, which was at the time the farm team of Efes. In the summer of 2012, Osman signed a professional contract with the senior team of Anadolu Efes.

Osman was born in the Republic of North Macedonia to an ethnic Turkish father and a Bosniak mother (from Novi Pazar, Serbia). He has an older brother, Caner, who is also a basketball player. He started playing basketball with KK Bosna's youth teams in 2001. In 2007, he moved to Anadolu Efes' junior teams after his outstanding performance at KK Bosna. Due to his paternal Turkish background, he became a Turkish citizen, as per Turkey's right-of-return laws. He has also represented the Turkish national basketball team since then.

Cedi Osman (born April 8, 1995) is a Turkish-North Macedonian professional basketball player for the Cleveland Cavaliers of the National Basketball Association (NBA). He plays the small forward position.