In team history, the Red Sox have seen 26 different pitchers win at least 20 games in a season at least once in a Boston uniform. The pitcher who holds the franchise record for the most victories in one season is Smoky Joe Wood, who won 34 games in 1912 for the eventual World Series champions; he was one of three pitchers on the 1912 staff, along with Buck O’Brien and Hugh Bedient, to reach the 20-win threshold, as the latter two each won exactly 20 games on a team that set the franchise record for wins in a season (105). Only one other pitcher in team history, Cy Young, won better than 30 games in a season; he accomplished this feat twice, once in Boston’s inagural season of 1901 (33) and then again in 1902 (32). Young also holds the record for the most seasons of 20 or more wins with the Red Sox, having accomplished the feat six times in the eight years that he was part of the starting rotation. After him, there are three pitchers with three seasons of 20 or more wins: Bill Dinneen (1902-1904), Luis Tiant (1973, 1974, 1976), and Roger Clemens (1986, 1987, 1990). Other multiple winners include Babe Ruth, Carl Mays, Boo Ferriss, Jesse Tannehill, Mel Parnell, Wood, Tex Hughson, and Wes Ferrell.
In total, there have been 46 instances where a pitcher won 20 games or more in a season for the Red Sox. Nine times, the starting rotation for Boston has had multiple 20-game winners. Between 1902 and 1904, Dinneen and Young won at least 20 games in each season for the Red Sox and, with Boston pitchers Tom Hughes (20 wins in 1903) and Tannehill (21 wins in 1904) also reaching that plateau, fans were witness to eight instances in three straight seasons that a Sox pitcher accomplished this feat. The most recent instance in which two players on the Red Sox pitching staff won at least 20 games in a single season happened just five years ago in 2002, when Derek Lowe (21) and Pedro Martinez (20) both managed the feat; before that, you have to go back to 1949 to find multiple 20-game winners on the Red Sox pitching staff for one season: Parnell (25) and Ellis Kinder (23). Curiously, there have been ten Boston pitchers in franchise history to fall just one win short of the mark for a single season; of those ten, both Martinez and Howard Ehmke did reach the mark in another season for the Sox. Martinez fell one win shy his first season with the club in 1998 but won 23 the next year, while Ehmke won 19 in 1924, one year after winning 20.