On March 12, 2018, Singleton initially announced that he would be retiring from the broadcasting booth after the 2018 season. However, on August 9, 2018, he announced that he had decided to postpone his retirement until after the 2019 season instead. During the Yankees-Rays broadcast on YES on September 25, 2019, Singleton announced he would be returning to the Yankees booth for the 2020 season. According to the New York Post, Singleton announced that he would be retiring after the 2021 season.