Connaughton's second season with the Bucks saw him again serve in a key bench role during the pandemic-shortened 2019-20 campaign. The fifth-year guard averaged 5.4 points, 4.2 rebounds and 1.6 assists while shooting 45.5 percent from the field, 33.1 percent from three, and 77.5 percent from the charity stripe. He reached double-digit points on nine occasions. The Notre Dame product also made an impact defensively, recording multiple steals or blocks 11 times. Connaughton scored a season-high 18 points in a win over the Trail Blazers on Nov. 21, adding four rebounds and two assists. On Nov. 30, Connaughton dished a season-high six assists to accompany six points and 10 rebounds in a win over the Hornets. He reached double-digit rebounds on three occasions, posting a season-high 11 on Dec. 27 against the Hawks. Connaughton went on to record his first career postseason double-double in the first round against Orlando, as he put up 15 points (courtesy of 5-of-8 three-point shooting) and 11 boards in Game 2 of that series. All in all, Connaughton averaged 4.0 points, 3.9 rebounds and 1.1 assists during the playoffs.2018
The 2018-19 season marked Connaughton's fourth in the league and first with the Bucks following a three-year stint with the Trail Blazers. He played 61 games and reached per-game career highs in minutes (20.7), points (6.9), rebounds (4.2) and assists (2.0). His points (12.0) and assists (3.5) per 36 minutes also represented career marks. Connaughton saw extended run during the final two months of the season, averaging 8.9 points, 6.0 rebounds and 2.1 assists across 27.0 minutes during March and April. One of his best games of the season came during that stretch, in a 14-point victory over the Rockets on Mar. 26. He posted 14 points, going 4-of-5 from deep, while also adding seven rebounds, four assists, two steals and two blocks in 31 minutes. Coach Mike Budenholzer continued to trust Connaughton during the Bucks' postseason run to the Eastern Conference Finals. In 15 appearances, he averaged 6.2 points, 6.2 rebounds and 1.4 assists in 21.6 minutes. During the first round of the playoffs against the Pistons, Connaughton posted an impressive 18 points, nine rebounds, four blocks and three assists during a 21-point, Game 2 victory.2017
Connaughton saw his role increase significantly in 2017-18, jumping a full 10.0 minutes per game up from the previous season. He appeared in all 82 games, starting five contests and averaging 5.4 points, 2.0 rebounds and 1.1 assists across 18.1 minutes. Connaughton shot 42.3 percent from the field, 35.2 percent from three and 84.1 percent from the charity stripe. His best performance was during the season opener in a 48-point victory over the Suns. Connaughton played 32 minutes and posted 24 points (9-14 FG, 4-7 3Pt, 2-2 FT), two rebounds and two assists. It was his lone 20-point effort, but he did manage 12 performances with at least 10 points. Connaughton also racked up seven efforts that included at least one made three, one rebound, one assist and one steal. His best shooting month of the season was April, with Connaughton posting a 76.0 true shooting percentage on the back of 10-of-16 shooting from the field, 4-of-9 shooting from deep and 1-of-1 shooting from the charity stripe across 100 total minutes. Under head coach Terry Stotts, the Trail Blazers finished 49-33 but lost in the first round of the postseason to the Pelicans. In the playoffs, Connaughton played 14.8 minutes per game, averaging 4.0 points, 1.5 assists and 1.0 rebounds.2016
A second-year pro, Connaughton saw his playing time increase a bit in his sophomore campaign. He saw action in 39 contests compared to just 34 in his rookie season, while his minutes nearly doubled to 8.1 per game. Although the sample size was small, Connaughton proved to be a remarkably efficient offensive player. He shot 51.4 percent from the field, including 51.5 percent from three-point range. Connaughton also displayed excellent ball security, averaging just 0.4 turnover per game. Seeing his role expand in Portland's final two regular-season games, Connaughton put forth his best two performances to date. He posted a career-high 15 points against the Spurs on April 10 before setting a new high-water mark with 19 points against New Orleans just two days later. Connaughton hit three shots from downtown in the game against San Antonio and connected on 5-of-10 from deep against the Pelicans. Clearly having earned the trust of the Portland coaching staff, Connaughton was called upon in three of the Blazers' four postseason games. In Game 2 against Golden State on April 19, Connaughton logged six rebounds in addition to a pair of assists.2015
Following four years at Notre Dame, Connaughton was selected with the 41st overall pick in the 2015 NBA Draft. He appeared in 34 games for the Trail Blazers during his age 23 rookie season. In 4.2 minutes per game, Connaughton averaged 1.1 points on 26.5 percent shooting. His best performance of the season was Mar. 11 during a 16-point loss to the Warriors. In 12 minutes, Connaughton posted seven points (3-6 FG, 1-2 3Pt), two assists and two rebounds. He saw the most minutes during an eight-point win over the Nuggets on Apr. 13. He played 29 minutes and recorded three points (1-6 FG, 1-4 3Pt), eight rebounds and one assist. Connaughton's season highs stood at, respectively, seven points (twice), eight rebounds, three assists and two steals. Under head coach Terry Stotts, Portland finished 44-38, defeating the Clippers in the first round of the playoffs before losing to the Warriors in the Western Conference Semifinals. Connaughton saw eight total minutes in the postseason. He recorded eight points and one rebound.
June 25, 2015Drafted by the Brooklyn Nets in the second round (41st pick) of the 2015 NBA Draft.
July 9, 2015Signed a three-year contract with the Portland Trail Blazers
August 1, 2018Signed a two-year contract as a free agent with the Milwaukee Bucks.
November 20, 2020Signed a three-year, $16 million contract with the Bucks.