Dotson signed a contract with the Cavaliers in late November before the 2020-21 season. He made his team debut Dec. 23 against the Hornets, posting one rebound and one steal in 13 minutes. He scored his first points with the team two games later, scoring five points against the 76ers. Overall, in Dotson's 46 appearances (seven starts), he averaged 6.7 points, 2.0 rebounds and 2.0 assists in 19.7 minutes. His best performance of the season was Jan. 9 against the Bucks. In 41 minutes, he recorded 21 points (8-17 FG, 2-7 3Pt, 3-3 FT), eight assists, two rebounds, one steal and one block with no turnovers. In his seven starts, Dotson averaged 13.0 points, 4.1 assists and 2.3 rebounds in 34.1 minutes. Dotson had 12 performances with double-digit points, four games with at least five rebounds and three games with at least five assists. On defense, he had 13 games with at least one steal and four games with at least one block. He hit his season-high three triples on four occasions.

The 2019-20 season was Dotson's third year with the Knicks. He appeared in 48 games for New York and averaged 6.7 points, 1.9 rebounds and 1.2 assists in 17.4 minutes per game. Dotson shot 41.4 percent from the field, hit 1.2 threes per contest at 36.2 percent from behind the arc and shot 66.7 percent from the free-throw line. Dotson set single-game season highs of 21 points, five rebounds, five assists, five threes, three steals and one block. Dotson's best overall performance of the campaign occurred Dec. 23 against the Wizards. In 27 minutes, he posted 19 points (7-13 FG, 5-10 3Pt, 0-2 FT), three assists and two rebounds with no turnovers. It was one of Dotson's 13 performances with at least 10 points. On Jan. 24, Dotson scored a season-high 21 points during a home loss to the Raptors. For the season, Dotson accumulated at least three assists in eight games and at least two rebounds in 26 games. Dotson grabbed at least one steal in 21 games and gathered one block in four games. Across the 11 games in which Dotson saw at least 24 minutes of playing time, he averaged 11.5 points, 1.9 rebounds and 1.4 assists per contest.

The 2018-19 season marked Dotson's second in the league and second with the Knicks. He played in 73 games, starting 40. He saw 27.5 minutes per game -- a boost of nearly 17 minutes from his rookie season -- and set career highs almost across the board as a result. Dotson averaged 10.7 points, 3.6 rebounds and 1.8 assists. He shot 41.5 percent from the field, 36.8 percent from distance and 74.5 percent from the free-throw line. As a starter, he averaged 12.2 points, 4.0 rebounds and 2.2 assists. He saw 40-plus minutes on six occasions, averaging 19.5 points, 5.2 rebounds and 3.5 assists in those instances. On Mar. 10, in an 11-point loss to the Timberwolves, Dotson arguably put on his best performance. He posted 26 points (10-19 FG, 4-9 3Pt, 2-2 FT), six assists, six rebounds and two steals across 41 minutes.

Damyean Dotson was drafted by the New York Knicks in the second round of the 2017 NBA Draft. Dotson split his rookie season between the Knicks and the G League Westchester Knicks. The rookie guard made his NBA debut Opening Night during a loss to the Thunder. Dotson would go on to appear in 17 of New York's first 25 games, while also joining Westchester for four November contests. On Nov. 28, while with Westchester, the guard posted 23 points, a trio of three-pointers and three rebounds in a loss versus Maine. He then spent most of December with New York. But, playing time with the parent club Knicks was hard to come by, and Dotson spent most of January with Westchester. On Jan. 17, Dotson scored a G League career-high 27 points to go with nine rebounds in a win over Long Island. Dotson played in 22 of New York's last 28 games. On Apr. 6, Dotson scored a career-high 30 points and grabbed 11 rebounds in a home win over the Heat. It was his second double-double of the season. In 44 games with the NBA club, Dotson averaged 4.1 points, 1.9 rebounds and 0.5 made threes over 10.8 minutes per game.