He started his professional career in 1889 with Canton, a professional minor league team. During his stint with Canton, he won 15 games and lost another 15 games.
In 1890, he signed contract with the Cleveland Spiders. On August 6 of the same year, he pitched a three-hit shutout during his major league debut. When he played matches for Cleveland Spiders, Chief Zimmer was his catcher in most of the games. The season of 1890 witnessed remarkable performance of Young. On the final day of the season, he won both games of a doubleheader.
The 1892 regular season proved to be a successful season for him. During the 1892 season, the National League started using a split season format. Though the Spiders won the second-half title, it was the Boston Beaneaters, the winner of the first-half title, who won the series. Though he pitched three games, yet he lost two decisions. In spite of his throwing of a complete game shutout, the game ended in a 0-0 tie.
In 1895, the Cleveland Spiders faced the Baltimore Orioles in the Temple Cup. In this series, the Cleveland’s victory in three matches helped it to win the Cup. During this time, he applied a new technique of pitching called ‘changeup’ to reduce stress on his arm.
In the following year, he lost a no-hitter with two outs in the ninth innings when Philadelphia Phillies’s Ed Delahanty hit a single.
He pitched the no-hitter for the first time in his career on September 18, 1897, in a match against the Cincinnati Reds.
When the Cleveland Spiders owner Frank Robison bought the St. Louis Browns, several top ranked players of the Spiders were transferred to St. Louis Browns. Cy Young was one of them and he played for St. Louis in the seasons of 1899 and 1900. During his two-year stint with St. Louis, he met Lou Criger, his favourite catcher.
After leaving St. Louis in 1901, he signed a $3,500 contract with Boston Americans of the American League. During his first year in American League, he acted as a pitcher to Lou Criger, who joined Boston Americans at the same time. In this year, he led the league that witnessed his electrifying performance for which he received AL Triple Crown for pitchers.
In 1903, the Boston Americans played against the Pittsburgh Pirates in the first modern World Series. The Bostons won the series by five games to three games.
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On May 2, 1904 after defeating Boston Americans, Philadelphia Athletics pitcher Rube Waddell challanged Young to face him so that he could repeat his performance against him. On May 5, 1904, Young pitched a perfect game against Waddell and the Philadelphia Athletics. It was the first perfect game in American League history.
Under his coaching the baseball team of Mercer University, won the Georgia state championship in 1903, 1904 and 1905.
In 1908, he pitched a no-hitter for the third time in his career. At the age of 41 years and three months, he was the oldest pitcher to record a no-hitter. The record stood for 82 years, until it was broken by the 43-year old Nolan Ryan.
In the 1910 season, he won his 500th career game while playing against Washington.
On September 22, 1911, he defeated Pittsburgh Pirates, 1–0; this was his last career victory.
He acted as manager of the Cleveland Green Sox of the Federal League in 1913.