Osman appeared in all 65 games for the Cavaliers during the coronavirus-shortened 2019-20 regular season, his third season with Cleveland. In October, Osman signed a four-year contract to stay with the Cavs. For the season, he averaged 11.0 points, 3.6 rebounds and 2.4 assists in 29.4 minutes per contest. He shot 43.7 percent from the field and hit career highs in both threes made per game (1.9) and three-point shooting percentage (38.3). Osman set a new single-game career high in rebounds (12) on Nov. 11 against the Nuggets and achieved the feat again Nov. 23 against the Trail Blazers. His other single-game season highs stood at 22 points, seven assists, four steals and one block. He posted two double-doubles. On Jan. 4, the 24-year-old scored a season-high 22 points during a home loss to the Thunder. Arguably his best overall game of the season occurred Jan. 25 against the Bulls. Osman posted 18 points (7-11 FG, 2-4 3Pt, 2-3 FT), six assists, two steals and one rebound in 30 minutes. His longest streak of double-digit scoring was six games from Oct. 28 through Nov. 8. During that six-game stretch, Osman averaged 10.8 points on 9.2 shots, 3.5 rebounds, 2.3 assists and 1.2 steals in 32.2 minutes per contest.

Given all the off-season changes that happened with the Cavaliers before the 2018-19 campaign, it's perhaps not surprising that Osman received a greatly increased role. Osman started 75 of the 76 games he played in during his sophomore season. His minutes also jumped considerably, from 11 minutes per game in 2017-18 to 32 minutes per contest this past season. The 6-foot-8 forward was a notable part of the offense, as he averaged 11.1 field goal and 4.9 three point attempts per contest. While his field goal and three pointer percentages both dropped, his free throw accuracy jumped considerably from 57 to 78 percent. The Macedonian-born forward put up 13.0 points per contest, but also showed a knack for making plays, distributing 2.6 assists per game. On Oct. 19, Osman dished out a career-high eight assists, to go with 22 points, in a home loss to the Timberwolves. On Jan. 25, Osman exploded for career-high 29 points against the Heat. On the season, Osman posted three double-doubles, 13 games with at least 20 points, 27 games with at least six boards, and 10 efforts with at least five assists. Defensively, he racked up 16 games with at least two steals and 10 games with at least one block.

Osman made his NBA debut in the 2017-2018 season after being a second-round pick by Cleveland in 2015 and spending some time overseas. The rookie mostly served as a reserve for the Cavaliers, appearing in 61 games and averaging 11.0 minutes per contest. Osman made his NBA debut on Oct. 20, during a brief appearance in a win at Milwaukee. He finished the season with averages of 3.9 points, 2.0 rebounds, 0.7 assists and 0.4 steals per game. Osman displayed some long-range skills in his bench role, shooting 36.8 percent from 3-point range on 87 attempts. Nearly half of all of his shots came from 3-point range, as Cleveland typically used Osman as a floor-spacer off the bench. However, he was effective when he did operate inside the arc, shooting 58.6 percent on his 2-point attempts. Though he mainly served as a reserve, the 22-year-old did make 12 starts as the Cavaliers dealt with injuries. Osman averaged 9.2 points, 3.5 rebounds and 2.0 assists across 23.4 minutes during those contests. He finished with a season-high 18 points in a start against the Knicks on April 11, a game in which he saw 39 minutes of action.