Gregory only began playing golf at the age of 27, when she married Leroy Gregory, a steel mill worker, who also enjoyed playing golf.
In 1939, when Leroy was drafted into the US Navy, she continued to work on her game and by the end of World War II was a proficient player. In 1950, at the age of 38, she began playing in tournaments.
In 1989, at the age of 76, and shortly after the death of Leroy, she won gold in the US Senior Olympics. She died shortly afterwards, with some 300 amateur tournament victories to her name.