The 2019-20 season marked Bledsoe's second full season with the Bucks. He recorded averages of 14.9 points, 5.4 assists, 4.6 rebounds and 1.3 combined steals-plus-blocks per game. The point guard shot 47.5 percent from the field, 34.4 percent from three and 79.0 percent from the charity stripe. During a win over the Timberwolves on Nov. 4, Bledsoe grabbed a season-high nine rebounds in addition to posting 22 points, six assists and one steal. Later in the month, Nov. 27 in a win over the Hawks, Bledsoe blocked a season-high two shots -- a mark he'd reach three more times. He also posted a season-high 10 assists in that contest, and he'd reach that mark three more times. During a victory over the Bulls on Dec. 30, Bledsoe swiped a season-high four steals while also recording 15 points, three assists and three rebounds. About a month later in a win over the Wizards on Jan. 28, Bledsoe scored a season-high 34 points while also contributing 10 assists, six rebounds and one steal. During the Bucks' first round playoff series against the Magic, Bledsoe averaged 11.6 points, 6.6 assists, 3.6 rebounds and 2.0 combined steals-plus-blocks. The next round against the Heat, Bledsoe averaged 11.8 points, 5.8 rebounds, 5.0 assists and 1.8 combined steals-plus-blocks. For the second straight season, Bledsoe was named to an All-Defensive team (second), and he posted the seventh-best defensive rating (103.8) in the NBA.

After coming over from Phoenix during the 2017-18 season, Bledsoe played his first full season with the Bucks in 2018-19. Playing alongside Giannis Antetokounmpo, Khris Middleton and Malcolm Brogdon, Bledsoe didn't need to score as much as he had in his four years with the Suns, though he did play in his most games (78) since the 2014-15 season. He averaged 15.9 points in 29.1 minutes and started every game he played for Milwaukee. Bledsoe maintained averages in rebounds (4.6) and assists (5.5), consistent with his career averages in those categories. He shot a career-high 48.4 field goal percentage. Bledsoe played great defense, recording 1.5 steals per game and earning his first NBA All-Defensive First Team selection. He recorded eight double-doubles and one triple-double in the campaign. Bledsoe's highest-scoring game came in a loss to Brooklyn on April 6, where the guard went for 33 points and added 11 assists, four rebounds, two steals and a block in 33 minutes. His triple-double was recorded on Feb. 27 in a win over Sacramento, where he totaled 26 points, 13 assists and 12 rebounds. He recorded multiple steals in 38 games, scored over 20 points 20 times, and handed out double-digit assists six times during the season.

Bledsoe began the 2017-18 season in Phoenix but played only three games for the Suns before being shipped to Milwaukee in early November. He immediately took over the starting point guard position and helped the Bucks earn their second straight playoff berth. Bledsoe's 17.8 points per game ranked third on the team while his 5.1 assists per game paced the squad. He also led Milwaukee in steals with 2.0 thefts per game - which placed him third-best in the league. Overall, Bledsoe enjoyed his finest shooting campaign as his 58.2 True Shooting Percentage and 53.6 Effective Field Goal Percentage represented the best marks of his career. He registered his fourth career triple-double in a win against Orlando on Apr. 9, tallying 20 points along with 12 rebounds and 11 assists. In a victory over the Lakers on Mar. 30, Bledsoe notched a season-high 39 points with seven three-pointers and complemented his scoring with six assists and four steals. The ex-Kentucky Wildcat followed his solid regular season with a strong showing in his first playoff series since 2012-13. Although the Bucks were eliminated in seven games by Boston in the first round, Bledsoe contributed per-game averages of 13.6 points, 3.6 rebounds and 3.7 assists. He put forth a valiant effort in Game 7 by draining 9-of-12 shots from the field and 4-of-4 from the free throw line on his way to 23 points.

Bledsoe enjoyed his best season to date during the 2016-17 campaign, despite being shut down March 16 due to knee soreness. The University of Kentucky product started all 66 games in which he played. Bledsoe scored 20 or more points on 34 separate occasions. That sample includes three tallies of 40 points or more. While his ability to fill up the stat sheet was certainly welcome, Bledsoe proved to be more than a one-trick pony. The 6-foot-1 guard had a pair of double-digit rebounding games. He also logged 10 or more assists six different times. He best all-around performance of the year may well have been a massive 25-point, 13-assist, 10-rebound triple-double in a big win over the Lakers on February 15. Defensively, Bledsoe averaged at least 1.4 steals (1.4) for a fifth consecutive season. Then, the emerging guard made good use of his visits to the free-throw line. Bledsoe shot a career-best 84.7 percent from the charity stripe.

Bledsoe's campaign was cut short after he suffered a torn meniscus the day after Christmas, which required season-ending surgery. He appeared in 31 games, starting each one and setting career highs in points (20.4), steals (2.0) and free-throw percentage (80.2). He also pitched in 6.1 assists and 4.0 rebounds and shot 45.3 percent from the field and 37.2 percent from deep. He shot especially well in 15 November games, going 27-of-61 (44.3 percent) from three. Bledsoe's best game of the season occurred Oct. 31 in an 11-point victory over the Trail Blazers. Across 38 minutes, he posted 33 points (12-21 FG, 2-6 3Pt, 7-9 FT), six assists, four steals, three rebounds and two blocks. That was one of his three 30-point efforts of the season. It was also one of his seven performances with at least five assists, one steal and one block. In addition, Bledsoe had a trio of double-doubles. He was also part of the Suns' most successful five-man group (minimum 50 minutes played). When Bledsoe was alongside Brandon Knight, PJ Tucker, Marcus Morris and Tyson Chandler, Phoenix was plus-4.7 points per 100 possessions. The Suns finished the season 23-59 and didn't make the playoffs.

The 2014-15 season marked Bledsoe's first injury-free campaign as a starter. During his second year with the Suns, the 25-year-old averaged 17.0 points, a career-high 6.1 assists and 5.2 rebounds, plus 1.6 steals across 34.6 minutes. He also found his way onto the NBA's leaderboards. Bledsoe ranked eighth in minutes played (2,800), 10th in both made free throws (353) and attempts (441), plus 13th in assists (493) and steals (127). Bledsoe finished the season with 13 double-doubles and two triple-doubles, plus three 30-point games, eight performances with 10-plus rebounds, nine games with 10-plus assists, and 21 efforts with three or more steals. Arguably his best game of the season occurred Mar. 21 in a 15-point victory over the Rockets on the road. Bledsoe posted 34 points (11-18 FG, 2-3 3Pt, 10-11 FT), eight rebounds, four assists, three steals and a block in 37 minutes. The Suns failed to make the playoffs, reaching a 39-43 record under head coach Jeff Hornacek. However, Bledsoe found himself a part of the team's most frequent five-man combination, which held a positive net rating of plus-6.5 points across a 391-minute sample. It also contained Goran Dragic, Markieff Morris, PJ Tucker and Alex Len.

After spending his first three seasons with the Clippers, Bledsoe was traded to the Suns on July 10, 2013. He proceeded to become a starter for the first time in his career, getting the nod in 40 of his 43 appearances. Though Bledsoe missed significant time with injury, he played well when healthy, setting career highs essentially across the board in his new, expanded role. He averaged 17.7 points, 5.5 assists, 4.7 rebounds and 1.6 steals in 32.9 minutes. Not only did he shoot at a higher volume, Bledsoe managed a career-high 57.8 true-shooting percentage. Bledsoe finished the year with four double-doubles, plus two 30-point games, three games with 10-plus assists, 28 performances with five-plus rebounds and 13 efforts with three or more steals. Arguably his best game of the season occurred Dec. 13 in a nine-point win over the Kings at home. Bledsoe played 35 minutes and posted 28 points (11-16 FG, 2-4 3Pt, 4-4 FT), eight assists, five rebounds, three steals and two blocks. Though the Suns finished the season 48-34 under head coach Jeff Hornacek, it wasn't enough for a postseason berth. Phoenix was 28-15 in games Bledsoe appeared in.

Bledsoe regained his footing in 2012-13 after appearing in just 40 games due to injury the year prior. The third-year point guard played in 76 games (12 starts), averaging career highs in points (8.5), true-shooting percentage (51.3), rebounds (3.0) and steals (1.4) while also contributing 3.1 assists across 20.4 minutes. He continued to establish himself as a defensive force behind starter Chris Paul, with Bledsoe ranking third in the NBA in steal percentage (3.7) and 16th in defensive box plus/minus (2.7). Bledsoe finished the year with two double-doubles, plus two 20-point games, two double-digit assist efforts and 12 games with at least three steals. His best performance of the season occurred Feb. 3 in a two-point loss to the Celtics on the road. Bledsoe posted 23 points (9-15 FG, 2-3 3Pt, 3-4 FT), 10 assists, seven rebounds, two steals and a block across 38 minutes. The Clippers finished the year 56-26 and played in the first round of the postseason, losing to the Grizzlies in six games. Bledsoe saw 16.2 minutes per game in the postseason, averaging 6.5 points, 3.0 assists and 2.5 rebounds. He led the Clippers in assists per 36 minutes (6.7). His best postseason effort was in a Game 1 victory, with Bledsoe racking up 15 points (7-7 FG, 1-2 FT), six rebounds and four assists in 18 minutes.

Bledsoe missed the first 17 games of the season due to a torn meniscus, and he ended up appearing in just 40 contests, not cracking the 20-minute mark in a single appearance until early April. It seemed like he struggled to get comfortable coming off the injury, and he averaged 3.3 points, 1.7 assists and 1.6 rebounds in 11.6 minutes. Bledsoe's best performance of the season occurred Mar. 14 in a 14-point victory over the Hawks at home. He posted 14 points (5-8 FG, 2-3 3Pt, 2-3 FT), four steals and two blocks across 17 minutes. The Clippers finished the season 40-26 and made it to the Western Conference Semifinals. The 2012 postseason marked the first of Bledsoe's career, and he came prepared. He appeared in all 11 games, seeing 17.2 minutes per contest and averaging 7.9 points on 58.7 percent shooting, plus 2.4 rebounds, 2.1 assists and 1.2 steals. Out of everyone on the Clippers in the playoffs, Bledsoe finished with the highest win shares per 48 minutes (.168) and tied Nick Young for the best offensive rating (114). Bledsoe's best game of the postseason was during Game 1 against the Spurs in the second round. In the 108-92 loss, Bledsoe posted 23 points (10-16 FG, 1-3 3Pt, 2-2 FT), five rebounds, four assists, three steals and one block in 27 minutes.

Following one season at Kentucky, Bledsoe was selected 18th overall in the 2010 NBA Draft and proceeded to play his rookie campaign for the Clippers. He earned Second Team All-Rookie honors, averaging 6.7 points, 3.6 assists, 2.8 rebounds and 1.1 steals in 22.7 minutes. Notably, Bledsoe finished with the NBA's 13th-best steal percentage (2.6). Bledsoe earned 25 starts in 81 appearances, and in those games, he averaged 8.9 points, 5.9 assists and 3.6 rebounds while totaling 29 steals and nine blocks. He finished with one double-double, plus two games with 20-plus points, 28 games with five-plus assists and nine games with three-plus steals. Arguably his best performance of the season occurred Mar. 5 in a six-point victory at home over the Nuggets. Bledsoe posted 20 points (7-11 FG, 2-5 3Pt, 4-5 FT), seven steals, four rebounds and three assists in 22 minutes. The Clippers finished the season 32-50 under head coach Vinny Del Negro.