Prior to the 2008 season, that was Gaylord Perry who went 24-16 in 1972.
Jim Bagby won 31 games for the Indians in 1920.
The Cleveland Browns had 11 wins in the 1995 season.
Cleveland Indians - 18 wins
The 1954 Cleveland Indians had 111 regular season wins. They were then swept in 4 straight in the World Series by the New York Giants.
In 2009 65 wins 97 losses.
Brandon Webb of the Arizona Diamondbacks and Cliff Lee of the Cleveland Indians led MLB in wins in 2008 with 22.
That was John Burkett with 22 wins and Bill Swift with 21 wins in the 1993 season.
In 1968, Detroit's Denny McLain recorded 31 wins; the most by any player since 1950. McLain was the last pitcher to reach 30 wins in a season.
In interleague play through the 2012 season, the Cubs and Indians are tied with 7 wins each.
Pitcher Mel Harder who spent 20 seasons (1928-1947) with the Indians. He ended up with career numbers of 223 wins, 186 losses, 3.80 ERA, 181 complete games, 25 shutouts, 3426 1/3 innings pitched, 1118 walks, and 1161 strikeouts. Hall of Fame pitcher Bob Feller (1936-1941, 1945-1956) is second with 18 seasons in an Indians uniform.
116 wins - 1906 Chicago Cubs and 2001 Seattle Mariners 114 wins - 1998 New York Yankees 111 wins - 1954 Cleveland Indians