"[2] As stated in Arthur Ashe's book, Hard Road to Glory, many observers called Gregory the best African-American female golfer of the 20th century.
[4] In 1948 Gregory won a tournament in Kankakee, Illinois, during which she defeated former United Golf Association champions Lucy Mitchell, Cleo Ball, and Geneva Wilson.
[5] Because she was African-American, Gregory was denied entry into the player's banquet at Congressional Country Club in Bethesda at the conclusion of the U.S. Women's Amateur in 1959.
[5] In 1989, at age 76 and competing against a field of 50 women, she won the gold medal in the U.S. National Senior Olympics, beating her competitors by 44 strokes.
[3] In 2000, the Urban Chamber of Commerce of Las Vegas began the Ann Gregory Memorial Scholarship Golf Tournament, which lasted seven years.