Cy Young: 192 wins
Legendary hurler Cy Young is tied with Roger Clemens as the Boston Red Sox all-time wins leader. Young is not only the Red Sox wins leader, but the all-time Major League wins leader with 511 in his 22-year career. The Hall of Famer spent his best seasons in Boston where he had a 2.00 ERA in 2,728.1 innings from 1901 to 1908. In his first three seasons in the American League, he won 33, 32, and 28 games for Boston, leading the league in each season. Cy Young put up dominant strikeout-to-walk numbers before it was in style, posting a 4.48 K/BB ratio in Boston. His most important wins, not included in this total, were the two he earned in Boston’s 1903 World Series Championship.
Roger Clemens: 192 wins
One of the greatest pitchers in recent history, Roger Clemens is tied with Cy Young for the Red Sox all-time wins record. With the Red Sox, Clemens won two of his record seven Cy Young Awards in addition to his 1986 AL MVP Award. He spent his first 13 seasons in Boston as one of the most dominant pitchers in the game and the Red Sox all-time strikeouts leader with 2,590. In his 24-year career, Clemens won 354 games and punched out 4,672 batters to rank among the top ten in Major League history in each category.
Tim Wakefield: 179 wins
One of the most successful knuckleballers in baseball history, active pitcher Tim Wakefield has climbed to third on the list of Boston Red Sox all-time wins leaders. Like Tiant, Wakefield revived his career in Boston and became one of the franchise’s legendary pitchers. 16 years into his tenure with the Red Sox, he has made more starts (404) and thrown more innings (2,826.1) than anyone in team history. He has won more than 15 games on four occasions, most recently in 2007 when he matched his career high with 17 wins. For his career as a whole, Wakefield has recorded 192 wins with more than 2,000 strikeouts in more than 3,000 innings.
Mel Parnell: 123 wins
Ranking fourth among Boston Red Sox all-time wins leaders, Mel Parnell was a great left-handed pitcher in the post-WWII era. Parnell spent his entire ten-year Major League career in Boston from 1947 to 1956. A two-time All-Star, Parnell posted a 3.50 ERA in 1,752.2 career innings. In 1949, he led the American League with 25 wins and 27 complete games, both of which were career highs.
Luis Tiant: 122 wins
Three-time All-Star Luis Tiant ranks fifth among Boston Red Sox all-time wins leaders. After arm injuries derailed his career in Cleveland, Tiant joined the Red Sox in 1971 and pitched for them through 1978. In eight seasons in Boston, El Tiante won 20 games three times with a 3.36 ERA in 1,774.2 innings. He established himself as a star of the Red Sox in 1972 when he led the American League with a 1.91 ERA and tossed six shutouts. Tiant was a fan favorite, a great comeback story, and one of the best pitchers in Red Sox history.