Matthews signed a two-year contract with the Bucks in July of 2019. He made his team debut during the first game of the season, a win over the Rockets on Oct. 24, posting 14 points, four rebounds, two steals, one block and one assist. He proceeded to score 14 points again in each of the next two games, totaling eight made threes across the first three contests of the season. About a month later, Nov. 25 in a win over the Jazz, Matthews scored a season-high 19 points. He would go on to reach that mark again in a win over the Pacers on Dec. 22. On Nov. 29 in a win over the Cavaliers, the veteran dished a season-high four assists. He would reach that mark again Feb. 20 in a win over the Pistons. In another win over the Cavaliers on Dec. 14, Matthews swiped a season-high three steals -- a mark he'd reach again in a win over the Lakers five days later. During a win over the Hornets on Mar. 1, Matthews grabbed a season-high eight rebounds, in addition to posting eight points, two assists and two steals. In the first round of the playoffs against the Magic, the shooting guard averaged 8.2 points, 1.8 rebounds and 1.6 assists. In the second round against the Heat, he averaged 6.2 points, 1.8 rebounds and 1.0 steals. Matthews' best overall playoff effort was Game 5 against Miami, as he recorded 11 points (3-6 FG, 0-3 3Pt, 5-6 FT), two steals, two blocks, one assist and one rebound with no turnovers.

Matthews began the 2018-19 season in Dallas, where he had spent the prior three campaigns. He appeared in 44 games (all starts) for the Mavericks, averaging 13.1 points, 2.3 rebounds and 2.3 assists in 29.8 minutes. On Jan. 31, he was traded to the Knicks. Matthews played just two games in New York, totaling 14 points, five assists, three rebounds, one steal and one block across 54 minutes. He was subsequently waived and picked up by the Pacers. With Indiana, he appeared in 23 games (all starts), averaging 10.9 points, 2.8 rebounds and 2.4 assists across 31.5 minutes. He also started all four playoff games for the Pacers, posting 7.0 points, 2.5 rebounds and 2.0 assists across 29.8 minutes. His season highs checked in at 25 points, seven rebounds, five assists, four blocks and three steals. Arguably his best game of the season occurred during a four-point loss to the Warriors on Dec. 12, when Matthews posted 25 points (including seven three-pointers), four assists, three rebounds and a steal in 36 minutes. He concluded the season with 10 games of at least 20 points.

Matthews wound up missing 18 of the final 19 games of the season due to a stress fracture in his right leg, but he played well in the 63 appearances (62 starts) he made. Across 33.8 minutes per game, the 31-year-old averaged 12.7 points, 3.1 rebounds, 2.7 assists and 1.2 steals. Matthews also drilled 2.4 threes per game at a 38.1 percent clip. He shot 40.7 percent from distance at home. His best shooting month of the season was February. In nine games, Matthews posted a 59.4 true shooting percentage, going 46-of-105 from the field, 29-of-68 from three and 9-of-10 from the charity stripe. Arguably his best performance of the season occurred Jan. 24 during a seven-point loss to the Rockets. In 38 minutes, Matthews recorded 29 points (10-18 FG, 7-14 3Pt, 2-2 FT), five assists, four rebounds, two steals and a block. That represented one of Matthews' seven games with at least 20 points, and he also made seven triples on three occasions. In addition, the veteran racked up 13 efforts with at least three made triples and two steals. The Mavericks finished the season 24-58 and did not make the playoffs.

The 2016-17 campaign marked Matthews' eighth season in the league and second year with the Mavericks. He averaged 13.5 points, 3.5 rebounds, a career-high 2.9 assists and 1.1 steals across 34.2 minutes. His 174 made threes and 479 three-point attempts ranked 17th and 13th, respectively, in the league. He was second on the Mavericks in total points (986), assists (210) and steals (77) while ranking first in made threes. November was Matthews' best three-point shooting month, as he went 40-of-92 (43.5 percent) from beyond the arc. His best game of the season was during a 112-92 win over the Nuggets at home Dec. 12. Matthews racked up 25 points (10-14 FG, 5-7 3Pt), four rebounds and two steals across 32 minutes. That was one of his 14 games with 20-plus points. He also posted 21 games with five-plus rebounds, 14 games with five-plus assists and nine games with at least three steals. The Mavericks, under head coach Rick Carlisle, went 33-49 and finished 11th in the Western Conference.

Matthews tore his Achilles in March of 2015 but vowed to be ready for the start of the 2015-16 season. The veteran made good on his promise, recovering in fewer than eight months to start and play 26 minutes in an opening night win over the Suns. Overall, Matthews appeared in 78 games, starting each one and averaging 12.5 points, 3.1 rebounds, 1.9 assists and 1.0 steal across 33.9 minutes. He ranked 10th in the NBA in three-pointers made with 189, and he ranked 18th in free-throw percentage (86.3). Matthews' best performance of the season took place Dec. 6 in a 12-point win over the Wizards. In 41 minutes, Matthews posted 36 points (12-23 FG, 10-17 3Pt, 2-2 FT), six rebounds, five assists, one steal and one block. It was his lone 30-point effort of the season, though Matthews did have nine performances with at least five made threes. One of Matthews' best stretches of the season occurred from Mar. 20 through Apr. 4. In those eight games, he averaged 17.6 points (44.6 FG%, 49.3 3P%, 85.0 FT%), 3.6 rebounds, 2.3 assists and 1.1 steals in 37.6 minutes. Under head coach Rick Carlisle, the Mavericks finished 42-40 but lost in the first round of the playoffs to the Thunder in five games. In the postseason, Matthews averaged 13.0 points, 3.6 rebounds, 1.2 assists and 1.2 steals in 34.6 minutes.

As a result of a torn Achilles tendon suffered in early March, Matthews played a career-low 60 games. Prior to suffering the injury, Matthews averaged 15.9 points, a career-high 3.7 rebounds, 2.3 assists and 1.3 steals in 33.7 minutes per game. He also drilled a career-high 2.9 threes per contest at a rate of 38.9 percent. His best three-point shooting month was December, with Matthews hitting 46 threes in 15 games at 41.4 percent. Matthews finished the season ranked ninth in made threes (173), eighth in effective field-goal percentage (56.3) and 13th in offensive box plus/minus (3.8). His best game of the season occurred Feb. 25 in a 111-95 win over the Spurs at home. In 34 minutes, Matthews posted 31 points (11-18 FG, 4-10 3Pt, 5-7 FT), five rebounds, three assists and three steals. That was Matthews' only 30-point effort of the season, though he finished the year with 14 performances of 20-plus points. He also racked up 21 games with at least five rebounds, seven games with five-plus steals, and nine efforts with at least three steals. Under head coach Terry Stotts, Portland finished the year 51-31 and lost to the Grizzlies in the first round of the playoffs.

After missing 13 games during the 2012-13 season, Matthews was back to his usual, healthy self in 2013-14. He started all 82 games, seeing 33.9 minutes per game. He averaged a career-high 16.4 points, a career-high 3.5 rebounds and 2.4 assists. Matthews also drilled a career-high 2.5 threes per contest at 39.3 percent. His 201 made threes ranked fifth in the NBA, and he ranked 14th in offensive rating (118.4), 17th in offensive win shares (6.3) and 17th in offensive box plus/minus (3.4). In a 13-point victory over the Wizards on Mar. 20, Matthews had his best performance of the season. He dropped 28 points (8-16 FG, 4-9 3Pt, 8-8 FT), five assists, one steal and one rebound across 33 minutes. It was one of his 24 efforts with 20-plus points. Matthews also posted 29 games with at least five rebounds, seven games with five or more assists and four efforts with at least three steals. Under head coach Terry Stotts, Portland finished the season 54-28 and made it to the second round of the playoffs against the Spurs after beating the Rockets. In the playoffs, Matthews averaged 14.5 points, 3.9 rebounds, 1.3 assists and 1.3 steals. His best postseason effort was in a 10-point loss to the Rockets during Game 5. Matthews played 39 minutes and recorded 27 points (9-18 FG, 5-9 3Pt, 4-4 FT), three blocks, two rebounds and one steal.

The 2012-13 season marked Matthews' fourth year in the league and third with the Trail Blazers. After suiting up for every game in his first three seasons in the league, Matthews missed 13 games due to hip and ankle injuries. In his 34.8 minutes per game, he averaged 14.8 points, 2.8 rebounds, a career-high 2.5 assists and 1.3 steals. Matthews also drilled a career-high 2.4 triples per game on 39.8 percent shooting (13th-best in the league). His 169 three-pointers made ranked 11th in the NBA. Matthews had his best game of the season Nov. 23 during a eight-point victory over the Timberwolves at home. He dropped 30 points (12-17 FG, 5-6 3Pt, 1-2 FT), four steals and three assists in 40 minutes. That marked one of his 18 performances on the season with 20-plus points, and it was his only 30-point effort. Under head coach Terry Stotts, the Trail Blazers finished the year 33-49 and did not make the postseason.

Matthews started 53 of the 66 games he appeared in during the lockout-shortened 2011-12 NBA season. He averaged 13.7 points, a career-high 3.4 rebounds, 1.7 assists and a career-high 1.5 steals across 33.8 minutes. Matthews finished fifth in the league in three-pointers made (129), 14th in steals (96) and 20th in free-throw percentage (86.0). His best game of the season was Apr. 2 during a five-point loss to the Jazz. Matthews posted 33 points (10-12 FG, 5-6 3Pt, 8-10 FT), three assists, two steals and one rebound across 40 minutes. That performance marked one of his two outings with at least 30 points. Under head coaches Nate McMillan (20-23) and Kaleb Canales (8-15), the Trail Blazers finished the season 28-38 and did not make the postseason.

Following a successful rookie year with the Jazz, who signed Matthews after he went undrafted, the Trail Blazers stepped in over the summer to sign him to a contract. He proceeded to start 69 of the 82 games he appeared in for Portland, setting career highs nearly across the board in his expanded role. Matthews averaged 15.9 points, 3.1 rebounds, 2.0 assists and 1.2 steals while shooting 44.9 percent from the field, 40.7 percent from three and 84.4 percent from the charity stripe. He ranked 12th in the NBA in three-point attempts (378) and seventh in makes (154). Matthews' best game of the season occurred Jan. 7 in a 10-point win over Minnesota on the road. He posted 36 points (10-18 FG, 7-10 3Pt, 9-9 FT), five rebounds, one assist and one steal in 40 minutes. It marked one of his four 30-point games on the season. Portland finished the season 48-34 under head coach Nate McMillan, but the Trail Blazers failed to make it out of the first round. In six playoff appearances, Matthews averaged 13.0 points, 1.2 rebounds and 1.0 assist across 33.7 minutes. He impressed during a Game 3 victory over the Mavericks, notably dropping 25 points on 4-of-6 from distance.

Following four collegiate seasons at Marquette, Matthews signed with the Jazz as a free agent after going unselected in the 2009 NBA Draft. He quickly established himself as a legitimate NBA talent, playing 20-plus minutes in all but 24 of the 82 games he appeared in. He also drew 48 starts. Overall, he averaged 9.4 points, 2.3 rebounds and 1.5 assists, notably shooting an efficient 48.3 percent from the field, 38.2 percent from three and 82.9 percent from the charity stripe. His best performance of the season was Mar. 14 during an eight-point loss to the Thunder on the road. Matthews posted 29 points (9-11 FG, 6-7 3Pt, 5-6 FT) and three rebounds across 35 minutes. It was one of his three efforts of 20-plus points. Utah finished the season 53-29 under head coach Jerry Sloan, making it to the second round of the postseason. Matthews was trusted heavily, playing 37.1 minutes per game in the playoffs, averaging 13.2 points, 4.4 rebounds, 1.8 steals and 1.7 assists. His best playoff performance was during an 11-point victory over the Nuggets during Game 4 of the first round. Matthews posted 18 points (7-11 FG, 1-3 3Pt, 3-4 FT), five rebounds, three assists, three steals and one block across 42 minutes.