Miami Heat (2015–2020) in October 2015 On June 26, 2015, Winslow was selected by the
Miami Heat with the 10th overall pick in the
2015 NBA draft. On July 3, 2015, he signed his rookie scale contract with the Heat. He made his debut for the team in their season opener against the
Charlotte Hornets on October 28, recording five points and seven rebounds off the bench in a 104–94 win. On November 6, he had a then season-best game with 13 points and eight rebounds in a loss to the
Indiana Pacers. On January 11, he made his first career start, recording seven points and three rebounds in a loss to the
Golden State Warriors. On February 22, he recorded a season-high 15 points, seven rebounds and four assists in 39 minutes off the bench in a 101–93 win over the Indiana Pacers. On March 14, he topped his season-high mark with 20 points in a 124–119 win over the
Denver Nuggets. During his rookie year, coach
Erik Spoelstra consistently called on Winslow to defend the most lethal attackers in the league, from
LeBron James to
James Harden, as he developed into a defensive stopper. At the season's end, he earned
NBA All-Rookie Second Team honors. Winslow started the Heat's first nine games of the 2016–17 season before missing the next 16 with a sore left wrist. On December 22, 2016, he had a season-best game with 23 points and 13 rebounds in a 115–107 win over the
Los Angeles Lakers, as he set a career high for points and tied a career best in rebounds. On January 5, 2017, Winslow was ruled out for the rest of the season after undergoing surgery to repair a torn labrum in his right shoulder. Winslow played in the first 27 games of the 2017–18 season but then missed 14 games with a knee strain. On February 5, he scored 16 points against the
Orlando Magic. On November 3, 2018, in his first start of the 2018–19 season, Winslow had 15 points, 10 rebounds and eight assists in a 123–118 loss to the
Atlanta Hawks. On December 10, he scored a career-high 28 points with six 3-pointers in a 108–105 loss to the
Los Angeles Lakers. After teammate and starting point guard
Goran Dragić suffered a right knee injury, Winslow was named as Miami's starting point guard in mid-December. On December 28, he posted 24 points, 11 rebounds, and seven assists in a 118–94 win over the
Cleveland Cavaliers. On January 10, he recorded a career-high 11 assists in a 115–99 win over the
Boston Celtics. Winslow played in only 11 games for the Heat during the 2019–20 season as he was sidelined with a back injury.
Memphis Grizzlies (2020–2021) On February 6, 2020, Winslow was acquired by the
Memphis Grizzlies in a three-team trade also involving the
Minnesota Timberwolves. On July 21, the Grizzlies announced that Winslow had suffered a
hip injury during team practice and would miss the rest of the 2019–20 season.
Los Angeles Clippers (2021–2022) On August 8, 2021, Winslow signed a two-year contract with the
Los Angeles Clippers.
Portland Trail Blazers (2022–2023) On February 4, 2022, Winslow was traded, alongside
Eric Bledsoe,
Keon Johnson, and a 2025 second-round pick, to the
Portland Trail Blazers in exchange for
Norman Powell and
Robert Covington. On December 21, 2022, during a 101–98 loss to the
Oklahoma City Thunder, Winslow exited the game with a left ankle injury. On December 26, the Trail Blazers announced that he had been diagnosed with a Grade 2 ankle sprain and would be re-evaluated in two weeks. After the All-Star break, Winslow received a second opinion on his injury and underwent a bone marrow aspirate concentrate procedure in March to address further discomfort in his left ankle. On March 29, he underwent season-ending left ankle surgery.
Raptors 905 (2023–2024) On October 20, 2023, Winslow signed with the
Toronto Raptors, but was waived the same day. On October 30, 2023, Winslow joined
Raptors 905. On February 10, 2024, Winslow signed a 10-day contract with Toronto, but didn't play for them. On February 20, he returned to Raptors 905.
Wisconsin Herd (2024–2025) On October 16, 2024, Winslow signed with the
Milwaukee Bucks, but was waived the next day. On October 28, he joined the
Wisconsin Herd. ==Career statistics==