She was born in Aberdeen Mississippi on July 25, 1912. When her family moved to Gary, Indiana, she began to play tennis and won the Gary City Championship at age 25. She learned to play golf from her husband, Leroy “Percy” Gregory.

In 1950, the year she began to compete in tournaments, she won six of them. She traveled to compete in events overseas, and in 1956 she became the first black woman to compete in a national championship (conducted by the USGA). It would be seven years before Althea Gibson would become the first black to play on the LPGA tour and nine years before Renee Powell of Canton Ohio (the only African American female Class A member of the PGA of America – this is her family) would begin her professional career as the second of three black women to play on the LPGA tour.

In 1989, at the age of 76, Ann Gregory beat all of the other players over 50 to win the gold medal  at the U.S. Senior Olympics. She would die the following year, with over 300 victories worldwide.

He was the first American-born golf professional (also the first American to compete in a U.S. Open) and the first African-American man to play in the U.S. Open. In 1895. He played in five more of them. His best finish was fifth in 1902. He tutored Walter J. Travis, who won the 1904 British Amateur Tournament, and competed in the United Golfers Association, a professional association for black players.

In 1931, he began work at the Shady Rest Golf Club, the first African-American course in the United States. He gave lessons, served as caddie master, repaired equipment, and provided greenkeeping consultations to other courses. He helped build golf courses in Maryland and Washington, D.C. He died in 1968. One of the clubs he made and played with is enshrined in the USGA museum.