After retiring as a baseball player, Singleton began his broadcasting career as a sportscaster for WJZ-TV in Baltimore in the mid-1980s and TSN in Canada, first as a color commentator on telecasts for the Toronto Blue Jays (1985 and 1986) and then as a television color commentator and as a radio play-by-play and color commentator for the Montreal Expos (1987–1996).

Currently, Singleton is a commentator for the New York Yankees on the YES Network and PIX 11, serving as both a color commentator and play-by-play announcer, along with partner and play-by-play announcer Michael Kay.
He also worked as an announcer for Yankee games on the MSG Network, before the inception of YES and joined the Yankees broadcasting team in 1997.

His trademark calls include "This one is gone" for a home run and "Look out!"
for a hard hit foul ball into the crowd or dugout, or when a pitch comes close to/hits a batter.
He will also occasionally call a pitch a "chuck and duck" for a ball hit right back toward the pitcher.
He also calls a pitch down the heart of the plate a "cookie".

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.
After retiring as a baseball player, Singleton began his broadcasting career as a sportscaster for WJZ-TV in Baltimore in the mid-1980s and TSN in Canada, first as a color commentator on telecasts for the Toronto Blue Jays (1985 and 1986) and then as a television color commentator and as a radio play-by-play and color commentator for the Montreal Expos (1987–1996).
Currently, Singleton is a commentator for the New York Yankees on the YES Network and PIX 11, serving as both a color commentator and play-by-play announcer, along with partner and play-by-play announcer Michael Kay. He also worked as an announcer for Yankee games on the MSG Network, before the inception of YES and joined the Yankees broadcasting team in 1997.
His trademark calls include "This one is gone" for a home run and "Look out!" for a hard hit foul ball into the crowd or dugout, or when a pitch comes close to/hits a batter. He will also occasionally call a pitch a "chuck and duck" for a ball hit right back toward the pitcher. He also calls a pitch down the heart of the plate a "cookie".
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.
Ken Singleton