During the 2019-20 season with the Bucks, Middleton was selected to his second consecutive All-Star game. In his 62 appearances, he averaged a career-high 20.9 points, a career-high 6.2 rebounds and 4.3 assists. He also reached career marks in every shooting category, hitting 49.7 percent of his field goals, 41.5 percent of his threes and 91.6 percent of his free throws. In the NBA ranks, Middleton finished 11th in three-point percentage, third in free-throw percentage, 12th in defensive rating (104.3), 15th in win shares (7.9), 16th in box plus/minus (4.1) and 19th in value over replacement player (2.9). On Dec. 21 in a win over the Knicks, Middleton swiped a season-high three steals, reaching that mark three more times during the campaign -- all in victories. About a month later, in a win over the Wizards on Jan. 28, Middleton scored a career-high 51 points to go along with 10 rebounds and six assists. Shortly after, on Feb. 8 in a win over the Magic, Middleton grabbed a season-high 13 rebounds to go with 21 points, six assists and two steals. Later, during the NBA bubble on Aug. 8 against the Mavericks, Middleton dished a season-high 11 assists in addition to posting 21 points and six rebounds. During the first round of the playoffs against the Magic, Middleton averaged 15.0 points, 7.8 rebounds and 5.2 assists. Against the Heat in the next round, the wing averaged 25.6 points, 6.8 assists, 6.0 rebounds and 1.4 steals. The Texas A&M product had his best playoff performance during Game 4 against Miami, racking up 36 points (12-28 FG, 3-7 3Pt, 9-9 FT), eight rebounds, eight assists and two steals.

Middleton suited up for his sixth season with the Bucks in 2018-19, arguably producing the best season of his career. He averaged 18.3 points per game -- the second-highest mark of his career -- to go along with career highs in rebounds (6.0), assists (4.3) and three-pointers made (2.3). Middleton also shot 44.1 percent from the field and 83.7 percent from the free-throw line. He improved on his three-point percentage from 2017-18, draining 37.8 percent of his attempts from beyond the arc. Middleton logged 31.1 minutes per contest in 77 appearances. Milwaukee lost in the Eastern Conference Finals to Toronto, but Middleton played and started in all 15 postseason games for the Bucks. In those games, he averaged 16.9 points, 6.3 rebounds, 4.4 assists and 2.7 threes. He shot 41.8 percent from the floor, 43.5 percent from three and 88.5 percent from the foul line. In the regular season and playoffs, Middleton finished with four games of at least 30 points, including a season-best 39-point effort on Mar. 28 in a win over the Clippers. He produced nine double-doubles, 40 games with at least three three-pointers made and 21 multi-steal games.

In his first full season following offseason hamstring injury, Middleton became a force in the Bucks lineup and solidifying himself as the No. 2 option on the team. The Texas A&M product started a career-best 82 games, averaging 20.1 points, 5.2 rebounds and 4.0 assists while playing 36.4 minutes per game. Middleton's 2,982 minutes played also marked the second highest total in the league for the year. He scored a career-high 43 points on Nov. 1 against Charlotte while adding five rebounds and seven assists. Middleton notched his first career triple-double with a 23-point, 10-assist, and career-high 14-rebound performance at Philadelphia on Jan. 20. He fell just shy of another triple-double when he tallied 20 points, nine assists and eight rebounds versus Boston on Apr. 3. Middleton also dropped 40 points and added nine boards against Phoenix on Nov. 22. His dominance over the Suns continued two months later when he poured in 35 points during a 109-105 victory. He matched a career-high with 11 assists against Cleveland on Nov. 7. He went on to average a career-high 24.7 points in the playoffs, including a 31-point, eight-rebound, six-assist effort in Game 1 against Boston and a 32-point performance in Game 7.

Although a hamstring injury limited Middleton to just 29 regular-season games this past season, he played exceptionally well. In 30.7 minutes per game, Middleton posted averages of 14.7 points, 4.2 rebounds and 3.4 assists. He also averaged at least 1.5 steals for the third time in four seasons. Middleton drained a career-high 43.3 percent of his threes while nailing 88.0 percent of his free throws. By comparison, Middleton's previous high-water mark from downtown was just 41.4 percent, which he set back in 2013-14. Fully healthy by the time the playoffs rolled around, Middleton averaged 14.5 points and 4.7 rebounds in Milwaukee's six-game, first-round loss to the Raptors.

Middleton stepped into a full-time starting role during the 2015-16 season. He got the nod in all 79 games that he appeared in, averaging career highs in points (18.2), assists (4.2) and steals (1.7). Middleton also ranked 13th in the NBA in steals (131) and eighth in free-throw percentage (88.8). He had his best game of the season Feb. 29 during a seven-point win over the Rockets. Across 44 minutes, Middleton racked up 30 points (7-10 FG, 1-3 3Pt, 15-15 FT), five steals, four assists, three rebounds and one block. It was one of his five 30-point games of the season. Middleton also racked up his lone double-double Mar. 12 during an 11-point win over the Pelicans. He posted 19 points (9-16 FG, 0-4 3Pt, 1-1 FT), 10 rebounds, eight assists and three steals in 41 minutes. That performance also marked one of Middleton's eight outputs with at least 20 points, five rebounds, five assists and one steal. He had one of his best stretches of the season from Feb. 22 to Mar. 4. Across six games, he averaged 25.0 points (51.6 FG%, 51.7 3P%, 92.5 FT%), 4.0 rebounds, 4.0 assists and 2.5 steals in 38.9 minutes. Under head coach Jason Kidd, the Bucks went 33-49 and did not make the postseason.

The 2014-15 season marked Middleton's third in the league and second with the Bucks. The 23-year-old started 58 of the 79 games he appeared in, averaging career highs in points (13.4), rebounds (4.4), assists (2.3) and steals (1.5) per game. He also posted a career-high 56.3 true shooting percentage. He ranked 11th in the NBA in three-point percentage (40.7), 16th in steal percentage (2.6) and 17th in total steals (122). His best game of the season was during a six-point victory over the Magic on Mar. 11. Middleton played 42 minutes and posted 30 points (12-17 FG, 4-4 3Pt, 2-2 FT), five assists, three rebounds and two steals. That marked one of his two 30-point efforts, and was one of his 10 performances with at least 20 points. Middleton also posted one double-double (points and rebounds), nine games with at least five assists, and 17 efforts with three or more steals. Under head coach Jason Kidd, the Bucks went 41-41 and made it to the postseason, though lost in the first round to the Bulls in six games. Middleton led the team in minutes during the playoffs (38.7 per game) and averaged a team-high 15.8 points, 3.7 rebounds, 2.3 steals and 2.0 assists. His best postseason effort was during a 94-88 Game 5 victory on the road, where he accumulated 21 points (8-16 FG, 2-4 3Pt, 3-3 FT), four rebounds, four steals and two assists across 38 minutes.

Middleton was dealt from the Pistons to the Bucks on Jul. 31. He saw his role expand with Milwaukee during his sophomore campaign, setting career highs nearly across the board. He started 64 of the 82 games he appeared in, averaging 12.1 points, 3.8 rebounds, 2.1 assists and 1.0 steals. His shooting splits were 44.0 percent from the field, 41.4 percent from three (12th-best in the NBA) and 86.1 percent from the charity stripe. During a 116-106 victory over the 76ers on Dec. 21, Middleton had his best performance of the season. He posted 27 points (11-15 FG, 1-5 3Pt, 4-4 FT), five rebounds, four assists, two steals and a block across 36 minutes. That marked one of his 12 games with at least 20 points, Middleton also posted at least five rebounds 26 times, at least five assists four times, and grabbed at least three steals seven times. Middleton's best shooting month was February, where he drilled 54.0 percent of his 50 three-point attempts. He saw the most run in April, garnering 35.3 minutes per game and averaging 14.8 points, 4.3 rebounds and 2.1 assists. Under head coach Larry Drew, the Bucks finished 15-67 and failed to make the postseason.

Following three seasons at Texas A&M, Middleton was selected by the Pistons with the 39th overall pick in the 2012 NBA Draft. He saw limited action with Detroit, appearing in 27 games, averaging 6.1 points, 1.9 rebounds and 1.0 assists. He also shot 44.0 percent from the field, 31.1 percent from distance and 84.4 percent from the charity stripe. Middleton's statistical highs were, respectively, 14 points, seven rebounds, four assists, four threes, two steals and one block. The most he played was 33 minutes, which was during a 99-85 victory over the Bulls on Apr. 7. Middleton posted 10 points (4-7 FG, 2-2 3Pt), three rebounds, two assists and two steals. Under head coach Lawrence Frank, the Pistons finished the season 29-53 and failed to make the postseason.