On November 3, 1986, while practicing for a seven-game series between Major League and Japanese All-Stars, Gedman was struck by a warmup pitch from Detroit Tigers pitcher Willie Hernández, resulting in a fractured cheekbone. This was the beginning of a litany of injuries, holdouts, and inconsistency which contributed to the waning of Gedman's skills, both offensive and defensive. In 1989, Rick Cerone replaced him as the regular Boston catcher. In 1990, he served as back-up catcher to Tony Peña, who was acquired by the Red Sox during the offseason. On June 7, Gedman was traded to Houston for a player to be named later.