Matthews chose to attend Marquette University despite being pressured to play for the University of Wisconsin–Madison like his father. Wesley was the biggest of the "three amigos", the three guards in the starting lineup for Marquette. This trio, Dominic James, Jerel McNeal, and Matthews, started nearly every game together from their first year onwards. With the lack of height in the 2008–09 season at Marquette, Matthews learned to play against bigger opponents and became one of the most dominant players in the nation driving to the basket. He grabbed 13 rebounds in a Marquette 48-point win over Division II opponent Lewis Flyers on December 28, 2005. In a game against the Tennessee Volunteers on December 16, 2008, Matthews scored a career-high 30 points, making 15 of 18 free throws. On January 7, 2009, he set a school record for field goal accuracy when he went 10-for-10 en route to 23 points in an 81–76 win over Rutgers.
On July 10, 2010, the Trail Blazers signed Matthews to a five-year, $34 million offer sheet. On July 21, 2010, following the Jazz's decision not to match the Trail Blazers' offer sheet, Matthews officially signed the five-year, $34 million contract. In his first season with Portland, Matthews averaged 15.9 points per game, and his three-point shot improved from 38 percent to 41 percent. After Brandon Roy began missing time due to knee problems, Matthews gained a spot in the Blazers' starting lineup. The durable Matthews played in 250 consecutive NBA games before being forced to sit out of a game on December 10, 2012, due to an injury to his left hip. Matthews' ability and willingness to play through minor injuries and pain earned him the nickname "Iron Man", an appellation used by Trail Blazers fans, television and radio commentators, and arena public address announcers alike. On November 23, 2013, in a game against the Golden State Warriors, Matthews was involved in an altercation and was ejected along with teammate, Mo Williams. He scored 23 points in 25 minutes of action before leaving the game. On November 25 it was announced that he was fined $20,000. On January 17, 2015, Matthews became the Trail Blazers all-time career leader in three-point field goals made, surpassing Terry Porter's franchise record of 773. On March 5, 2015, in a game against the Dallas Mavericks, Matthews tore his left achilles tendon and was subsequently ruled out for the rest of the season.
Dallas Mavericks (2015–2019)
On July 9, 2015, Matthews signed a four-year deal with the Dallas Mavericks. On December 6, 2015, he scored 28 of his season-high 36 points in the second half of the Mavericks' 116–104 win over the Washington Wizards. He hit 10 three-pointers in the game, with eight of them coming in the second half. On November 30, 2016, Matthews scored a season-high 26 points in a 94–87 loss to the San Antonio Spurs. He tied that mark three times in early December. Matthews set a new season high on February 3, 2017, scoring 27 points in a 108–104 win over the Portland Trail Blazers. On November 18, 2017, Matthews scored a season-high 22 points in a 111–79 win over the Milwaukee Bucks. On December 8, 2017, he set a new season high with 29 points in a 109–102 loss to Milwaukee. On January 24, 2018, he matched a pair of season highs with 29 points and seven 3-pointers in a 104–97 loss to the Houston Rockets. On February 13, 2018, in a 114–109 loss to Sacramento Kings, Matthews became the seventh Dallas player to hit 500 3-pointers with the team. On April 30, 2018, Matthews exercised his player option for the 2018–19 season. In January 2019, Matthews became the sixth player in Mavericks history to make 600 3-pointers, and the first undrafted player in NBA history to make 1,500 3-pointers.
On January 31, 2019, Matthews was traded to the New York Knicks in a multiplayer trade. On February 7, Matthews was waived by the Knicks after appearing in just two games for the team.
On February 10, 2019, Matthews signed with the Indiana Pacers. On February 22, Matthews made 6 three-pointers and finished with 24 points, to lead the Pacers in a comeback win over the New Orleans Pelicans.
Milwaukee Bucks (2019–present)
On July 12, 2019, Matthews signed with the Milwaukee Bucks.
