 Bayless sat out the start of the 2018–19 season to rehabilitate a hyperextended right knee.On November 12, 2018, Bayless was traded to the Minnesota Timberwolves, along with Robert Covington, Dario Šarić and a 2022 second-round pick, in exchange for Jimmy Butler and Justin Patton.He made his season debut on December 21 against the San Antonio Spurs.