The first version of softball was invented in Chicago, Illinois on Thanksgiving Day, 1887 by George Hancock as a winter version of baseball. It was intended to be a way for baseball players to keep in practice during the winter. At the time, the sport was called "Indoor Baseball".

Yale and Harvard alumni had gathered at the Farragut Boat Club in Chicago to hear the score of the annual football game. When the score was announced and bets were paid, a Yale alumnus threw a boxing glove at a Harvard supporter. The other person grabbed a stick and swung at it. Hancock called "Play ball!" and the game began. Hancock took a boxing glove and tied it into a ball. A broom handle was used as a bat. The first softball game ended with a score of 44-40. The ball, being soft, was fielded barehanded rather than with gloves like those which had been introduced to baseball in 1882. Hancock developed a ball and an undersized bat in the next week. The Farragut Club soon set rules for the game, which spread quickly to outsiders. The game, under the name of "Indoor-Outdoor", was moved outside next year, and the first rules were published in 1889.

In 1895 Lewis Rober, Sr. of Minneapolis organized outdoor games as exercise for firefighters; this game was known as kitten ball (after the first team to play it), pumpkin ball, or diamond ball. Rober's version of the game used a ball 12 inches (305 mm) in circumference, rather than the 16-inch (406 mm) ball used by the Farragut club, and eventually the Minneapolis ball prevailed, although the dimensions of the Minneapolis diamond were passed over in favor of the dimensions of the Chicago one. Rober may not have been familiar with the Farragut Club rules. The first softball league outside the United States was organized in Toronto in 1897.

The name "softball" dates back to 1926. The name was coined by Walter Hakanson of the YMCA at a meeting of the National Recreation Congress. (In addition to "indoor baseball", "kitten ball", and "diamond ball", names for the game included "mush ball", "pumpkin ball," and "cabbage ball".) The name softball had spread across the United States by 1930. By the 1930s, similar sports with different rules and names were being played all over the United States and Canada. The formation of the Joint Rules Committee on Softball in 1934 standardized the rules and naming throughout the United States.

Sixteen-inch softball, also sometimes referred to as "mush ball" or "super-slow pitch", is a direct descendant of Hancock's original game. Defensive players are not allowed to wear fielding gloves; however, a 16-inch softball is actually soft, and can be fielded safely with bare hands. Sixteen-inch softball is played extensively in Chicago and New Orleans. In New Orleans, sixteen-inch softball is called "Cabbage Ball" and is a popular team sport in area elementary and high schools.

By the 1940s, fast pitching began to dominate the game. Although slow pitch was present at the 1933 World's Fair, the main course of action taken was to lengthen the pitching distance. Slow pitch achieved formal recognition in 1953 when it was added to the program of the Amateur Softball Association, and within a decade had surpassed fast pitch in popularity.

Softball was introduced to the United Kingdom in 1972 when the movie A Touch of Class was being filmed in London. The first British women's softball league was established in 1983.

In 1977, the American Professional Slow Pitch League (APSPL) became the first of three men's professional softball leagues to play between 1977 and 1982. The Detroit Caesars were the first team to win a professional softball World Series.

In 1991, women's fast-pitch softball was selected to debut at the 1996 Summer Olympics. The 1996 Olympics also marked a key era in the introduction of technology in softball; the IOC funded a landmark biomechanical study on pitching during the games.

In 2002, sixteen-inch slow pitch was written out of the ISF official rules, although it is still played extensively in the United States under Amateur Softball Association of America, or ASA rules.

The 117th meeting of the International Olympic Committee, held in Singapore in July 2005, voted to drop softball and baseball as Olympic sports for the 2012 Summer Olympic Games.
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