During his 22-year career, Young recorded numerous professional pitching records in the majors, some of which have stood for a century. Young retired with 511 career wins, 94 wins ahead of Walter Johnson, who is second on the list of most wins in Major League history. In honor of Young's contributions to Major League Baseball, the Cy Young Award, an annual award given to the pitcher voted the most effective in each of the two leagues, was created in 1956. Young was also elected to The Baseball Hall of Fame in 1937.
In addition to wins, Young currently holds the Major Leagues records for most career innings pitched (7,355), most career games started (815), and most complete games (749). He also retired with 316 losses, the most in MLB history. Over the span of his career, Young had 76 career shutouts, which is the fourth most in history. He also won at least 30 games in a season five times, with ten other seasons of 20+ wins. In addition, Young pitched three no-hitters, including the first perfect game of baseball's "modern era". In 1999, 88 years after his final Major League appearance and 44 years after his death, editors at The Sporting News ranked Cy Young 14th on their list of "Baseball's 100 Greatest Players". That same year, baseball fans named Young to the Major League Baseball All-Century Team.
Young's career started in 1890 with the Cleveland Spiders. After eight years with the Spiders, Young was moved to St. Louis in 1899. After two years there, Young jumped to the newly-created American League, joining the Boston franchise. He was traded back to the city of Cleveland in 1909, before spending the final two months of his career in Boston. After his retirement, Young went back to his farm in Ohio, where he stayed until his death at age 88 in 1955.
Franchises in the National League, the major professional sports league at the time, wanted the best players available to them. Therefore, in , Young signed with the Cleveland Spiders, a team which had moved up from the American Association to the National League the previous year.
Early on, Young established himself as one of the harder-throwing pitchers in the game. Bill James wrote that Zimmer often put a piece of beefsteak inside his baseball glove to protect his catching hand from Young's fastball. In the absence of radar guns, however, it is difficult to say just how hard Young actually threw. Young continued to perform at a high level during the 1890 season. On the last day of the season, Young won both games of a doubleheader. In the first weeks of Young's career, Cap Anson, the player-manager of the Chicago Colts spotted Young's ability. Anson told Spiders' manager Gus Schmelz, "He's too green to do your club much good, but I believe if I taught him what I know, I might make a pitcher out of him in a couple of years. He's not worth it now, but I'm willing to give you $1,000 for him." Schmelz replied, "Cap, you can keep your thousand and we'll keep the rube."
Two years after Young's debut, the National League moved the pitcher's position back by five feet. Since , pitchers had pitched within a "box" whose front line was 50 feet from home base, and since they had been compelled to toe the back line of the box when delivering the ball. The back line was 55 feet, six inches away from home. In 1893, five feet was added to the back line, yielding the modern pitching distance of 60 feet, six inches. In the book The Neyer/James Guide to Pitchers, sports journalist Rob Neyer wrote that the speed with which pitchers like Cy Young, Amos Rusie, and Jouett Meekin threw was the impetus that caused the move.
The regular season was a success for Young, who led the National League in wins (36), ERA (1.93), and shutouts (9). Just as many contemporary Minor League Baseball leagues operate today, the National League was using a split season format during the 1892 season. The Boston Beaneaters won the first-half title, and the Spiders won the second-half title, with a best-of-nine series determining the league champion. Despite the Spiders' second half run, the Beaneaters swept the series, five games to none. Young pitched three complete games in the series, but lost two decisions. He also threw a complete game shutout, but the game ended in a 0–0 tie.
The Spiders faced the Baltimore Orioles in the Temple Cup, a precursor to the World Series, in . Young won three games in the series and Cleveland won the Cup, four games to one. It was around this time that Young added what he called a "slow ball" to his pitching repertoire, to reduce stress on his arm. The pitch today is called a changeup.
In , Young lost a no-hitter with two outs in the ninth inning when Ed Delahanty of the Philadelphia Phillies hit a single. On September 18, 1897, Young pitched the first no-hitter of his career in a game against the Cincinnati Reds. Although Young did not walk a batter, the Spiders committed four errors while on defense. One of the errors had originally been ruled a hit, but the Cleveland third baseman sent a note to the press box after the eighth inning, saying he had made an error, and the ruling was changed. Young later said, that, despite his teammate's gesture, he considered the game to be a one-hitter.
The Boston Americans played the Pittsburgh Pirates in the first modern World Series in . Young, who started Game One against the visiting Pirates, thus threw the first pitch in modern World Series history. The Pirates scored four runs in that first inning and Young lost the game. Young performed better in subsequent games, winning his next two starts. He also drove in three runs in Game Five. Young finished the series with a 2–1 record and a 1.85 ERA in four appearances, and the Boston Americans defeated the Pittsburgh Pirates, five games to three games.
After one-hitting Boston on May 2, 1904, Philadelphia Athletics pitcher Rube Waddell taunted Young to face him so that he could repeat his performance against Boston's ace. Three days later, Young pitched a perfect game against Waddell and the Athletics. It was the first perfect game in American League history. Waddell was the 27th and last batter, and when he flied out, Young shouted, "How do you like that, you hayseed?" Waddell had picked an inauspicious time to issue his challenge. Young's perfect game was the centerpiece of a pitching streak. Young set major league records for the most consecutive scoreless innings pitched and the most consecutive innings without allowing a hit; the latter record still stands at 24.1 innings, or 73 hitless batters. Even after allowing a hit, Young's scoreless streak reached a then-record 45 shutout innings. Before Young, only two pitchers had thrown perfect games. This occurred in , when Lee Richmond and John Ward pitched perfect games within five days of each other, although under somewhat different rules: the front edge of the pitcher's box was only 45 feet from home base (the modern release point is about 10 feet farther away); walks required eight balls; and pitchers were obliged to throw side-armed. Young's perfect game was the first under the modern rules established in 1893. One year later, on July 4, 1905, Rube Waddell beat Young and the Americans, 4–2, in a 20-inning matchup. Young pitched 13 consecutive scoreless innings before he gave up a pair of unearned runs in the final inning. Young did not walk a batter and was later quoted: "For my part, I think it was the greatest game of ball I ever took part in." In 1907, Young and Waddell faced off in a scoreless 13-inning tie.
In , Young pitched the third no-hitter of his career. Three months past his 41st birthday, Cy Young was the oldest pitcher to record a no-hitter, a record which would stand 82 years until 43-year-old Nolan Ryan surpassed the feat. Only a walk kept Young from his second perfect game. After that runner was caught stealing, no other batter reached base. At this time, Young was the second-oldest player in either league. In another game one month before his no-hitter, he allowed just one single while facing 28 batters. On August 13, 1908, the league celebrated "Cy Young Day." No American League games were played on that day, and a group of All-Stars from the league's other teams gathered in Boston to play against Young and the Red Sox.
Young was traded back to Cleveland, the place where he played over half his career, before the 1909 season, to the Cleveland Naps of the American League. He split , his final year, between the Naps and the Boston Rustlers.
On September 22, 1911, Young shut out the Pittsburgh Pirates, 1–0, for his last career victory. In his final start two weeks later, the last eight batters of Young's career combined to hit a triple, four singles and three doubles.
Cy Young's career is seen as a bridge from baseball's earliest days to its modern era; he pitched against stars such as Cap Anson, already an established player when the National League was first formed in 1876, as well as against Eddie Collins, who played until 1930. When Young's career began, pitchers delivered the baseball underhand and fouls were not counted as strikes. The pitcher's mound was not moved back to its present position of 60 feet, six inches until Young's fourth season; he did not wear a glove until his sixth season.
Young led his league in wins five times (1892, 1895, and 1901–1903), finishing second twice. His career high was 36 in 1892. He had fifteen seasons with twenty or more wins, two more than the runners-up, Christy Mathewson and Warren Spahn. Young won two ERA titles during his career, in 1892 (1.93) and in 1901 (1.62), and was three times the runner-up. Young's earned run average was below 2.00 six times, but this was not uncommon during the dead ball era. Although Young threw over 400 innings in each of his first four full seasons, he did not lead his league until 1902. He had 40 or more complete games nine times. Young also led his league in strikeouts twice (with 140 in 1896, and 158 in 1901), and in shutouts seven times. Young led his league in fewest walks per nine innings thirteen times and finished second one season. Only twice in his 22-year career did Young finish lower than 5th in the category. Although the WHIP ratio was not calculated until well after Young's death, Young was the retroactive league leader in this category seven times and was second or third another seven times. Cy Young is tied with Roger Clemens for the most career wins by a Boston Red Sox pitcher. They each won 192 games while with the franchise.
Particularly after his fastball slowed, Young relied upon his control. Young once quoted as saying, "Some may have thought it was essential to know how to curve a ball before anything else. Experience, to my mind, teaches to the contrary. Any young player who has good control will become a successful curve pitcher long before the pitcher who is endeavoring to master both curves and control at the same time. The curve is merely an accessory to control." In addition to his exceptional control, Young was also a workhorse who avoided injury. For nineteen consecutive years, from 1891 through 1909, Cy Young was in his leagues' top ten for innings pitched; in fourteen of the seasons, he was in the top five. Not until 1900, a decade into his career, did Young pitch two consecutive incomplete games. By habit, Young restricted his practice throws in spring training. Young quoted on this,"I figured the old arm had just so many throws in it," said Young, "and there wasn't any use wasting them." Young once described his approach before a game:
"I never warmed up ten, fifteen minutes before a game like most pitchers do. I'd loosen up, three, four minutes. Five at the outside. And I never went to the bullpen. Oh, I'd relieve all right, plenty of times, but I went right from the bench to the box, and I'd take a few warm-up pitches and be ready. Then I had good control. I aimed to make the batter hit the ball, and I threw as few pitches as possible. That's why I was able to work every other day."
By the time of his retirement, Young's control had slipped. Young had also gained weight. In three of his last four years, he was the oldest player in the league.
Cy Young was also mentioned in the poem "Lineup for Yesterday" by Ogden Nash, which was published in Sport magazine in January 1949. The poem paid tribute to baseball players, as well as Nash's own fanaticism, and was formatted in an alphabetical list.
In 1956, about one year after Young's death, The Cy Young Award was created. The first award was given to Brooklyn's Don Newcombe. Originally, it was a single award covering the whole of baseball. The honor was divided into two Cy Young Awards in 1967, one for each league.