The first Women's Air Derby on August 13-20, 1929, was a transcontinental race as part of the National Air Races at Cleveland that was entered by 20 women flyers. While at the time there were 70 US-licensed women pilots, only 40 met the race requirements of having 100 hours of solo flight, including 25 hours of solo cross-country, a license from the Federation Aeronautique Internationale (FAI), and an annual sporting license issued by the National Aeronautics Association (NAA). Of that group, there were 20 entrants in the Derby.

    It took eight days to fly and navigate the route using only dead reckoning and road maps. Louise Thaden came in first, and 14 others who completed the race in one of the two aircraft categories were Amelia Earhart, Ruth Elder, Edith Foltz, Mary Haizlip, Jessie Keith-Miller, Opal Kunz, Blanche Noyes, Gladys O'Donnell, Phoebe Omlie, Neva Paris, Thea Rasche, Bobbi Trout (out of the competition with two forced landings), Mary von March, and Vera Dawn Walker.

    1929 was also the year the Ninety-Nines women's aviation organization was born, which would enter this picture 18 years later.

Although women were not allowed to compete in major air races until the 1930s, many events created separate divisions for them which were identical to the men's divisions, and it was soon noted that the women's times and speeds were very close to those of the men's. Women were encouraged to hold their own competitions, such as the Women's International Free-For-All, the 1934 Dixie Derby from Washington DC through the southern states up to Chicago, and the Women's National Air Meet held in August 1934 at Dayton.

    Occasionally women were allowed to compete with men, like the National Air Races' Transcontinental Handicap Air Derby, but any accident gave race officials one more excuse to exclude women, as in the case of Florence Klingensmith's fatal crash in a Gee Bee Y during the 1933 Phillips Race in Chicago—it was the reason given for excluding women from the 1934 Bendix Race.

    However, women finally gained deserved headlines when Louise Thaden and Blanche Noyes won the prestigious 1936 Bendix Race in their Beechcraft C-17R. Then Laura Ingallas crossed the finish line 45 minutes later in her Lockheed Orion to take second place, and Amelia Earhart and Helen Richey finished fifth.

After World War 2, one focus of the Ninety-Nines was a revival of the women's air races. 1947 saw the first of the All-Woman Air Races, from Palm Springs CA to Tampa FL. That year the race had only two contestants; the next year there were seven. The 1948 and 1949 Jacqueline Cochran All-Woman Transcontinental Air Races (AWTAR) were the formal beginning of what would become popularly known as the Powder Puff Derby, a reference to the 1929 Women's Air Derby by humorist and aviation advocate Will Rogers.

    The AWTAR became a major event with its own office and a nine-woman board of directors that spent a year preparing for each race. Safety was always a priority and, gradually over the years, the message was clear... women are good pilots. During the '60s, the Ninety-Nines also embraced the All-Woman's International Air Race, or "Angel Derby." The final AWTAR was held in 1977, ended because of rising costs, diminished corporate sponsorship, and air traffic congestion.