regulation as Middleton hit a contested game-winning buzzer beater to defeat the Suns, 96–94, with Middleton finishing with 14 points. On March 7, 2015, he scored a then-career-high 30 points on 11-of-20 shooting in a 91–85 win over the Washington Wizards. In his second season with the Bucks, Middleton emerged as an important "3-and-D" player, shooting 46.7 percent from the floor and 40.7 percent from behind the three-point arc. He averaged 13.4 points, 4.4 rebounds and 2.3 assists per game. 2015–16 season: New contract On July 9, 2015, Middleton re-signed with the Bucks to a five-year, $70 million contract, with a player option for the fifth year. This constituted a significant pay raise for Middleton, as he earned $915,000 the prior year. On December 29, 2015, in a loss to the Oklahoma City Thunder, he scored a career-high 36 points on 13-of-22 from the field and 6-of-9 from three-point range. On March 4, 2016, in a win over the Minnesota Timberwolves, he scored 32 points on 11-of-16 shooting, including 8-of-9 on three-pointers, marking the most three-pointers made by a Bucks player since Carlos Delfino had eight on March 18, 2011. He tied his career high of 36 points on April 10, 2016, in a 109–108 overtime win over the Philadelphia 76ers. 2016–17 season: Injury and surgery On September 21, 2016, Middleton was ruled out for six months after sustaining a left hamstring injury in preseason workouts that required surgery. On February 8, 2017, he made his season debut after missing the first 50 games with the hamstring injury, scoring five points in 15 minutes in a 106–88 loss to the Miami Heat. On March 17, 2017, he scored 14 of his season-high 30 points in the fourth quarter of the Bucks' 107–103 win over the Los Angeles Lakers. 2017–18 season: Breakthrough On November 1, 2017, Middleton scored a then career-high 43 points in a 126–121 loss to the Charlotte Hornets. On November 22, 2017, he scored 40 points in a 113–107 overtime win over the Phoenix Suns. On January 20, 2018, he had his first career-triple double with 23 points, 14 rebounds and 10 assists in a 116–94 loss to the Philadelphia 76ers. In Game 1 of the Bucks' first-round playoff series against the Boston Celtics, Middleton had 31 points, eight rebounds and six assists in a 113–107 overtime loss. The Bucks went on to lose the series in seven