On July 9, 2014, Uehara was named to his first career All-Star Game, replacing injured New York Yankees pitcher Masahiro Tanaka. He struggled near the end of the 2014 regular season and was removed from the closer role on September 5. He signed a two-year extension with the Red Sox on October 30, 2014, after finishing the regular season with a 6–5 record, 2.52 ERA, 80 strikeouts in 64 1/3 innings, and 26 saves in 31 opportunities as the Red Sox failed to defend its title by finishing with a subpar 71-91 record. Uehara returned to the closer position in the 2015 season, but on August 7, he suffered a season-ending injury when a batted ball struck his right wrist. He would prematurely end his 2015 campaign with a 2–4 record added by a 2.23 ERA, 47 strikeouts in 40 1/3 innings, and 25 saves in 27 attempts as the Red Sox failed to reach the .500 mark for the 2nd season in a row. In 2016, Uehara finished the regular season with a 2–3 record, a 3.45 ERA, 63 strikeouts in 47 innings, and 7 saves after spending some time on the disabled list with a pectoral strain. His team would make the postseason for the first time since the 2013 championship season. In the 2016 ALDS, Uehara pitched 2 games without allowing a run in 2 innings but the Red Sox got swept by the Cleveland Indians in 3 games.