On July 9, 2015, Shumpert re-signed with the Cavaliers to a four-year, $40 million contract. On September 29, 2015, he was ruled out for three months after suffering a ruptured Extensor Carpi Ulnaris sheath in his right wrist. He made his season debut on December 11 against the Orlando Magic, scoring 14 points off the bench in a 111–76 win. On March 5, 2016, he recorded 12 points and a career-high 16 rebounds off the bench in a 120–103 win over the Boston Celtics. On April 11, he was ruled out for the Cavaliers' final two games of the regular season after getting his left knee drained. Shumpert returned in time for the playoffs and helped the Cavaliers make it the NBA Finals for the second straight season. The Cavaliers would again face the Golden State Warriors. Despite the Cavaliers going down 3–1 in the series following a Game 4 loss, they went on to win the series in seven games to become the first team in NBA history to win the championship after being down 3–1.