After graduating in 1906, Glaze signed with the Boston Americans, as the press referred to them in 1906. The team would later be known as the Boston Red Sox. Over three years, Glaze posted a record of 15 wins against 21 losses, with 137 strikeouts and a 2.89 earned run average in 61 games and 340 innings pitched. A career highlight took place on August 31 of his rookie year, when he outdueled Philadelphia Athletics star pitcher Rube Waddell. Glaze began coaching in the offseasons, starting as a 1906 football assistant at Dartmouth; he also helped coach their baseball team in 1908. He left the Red Sox following the 1908 season, and spent the next several years with a number of minor league teams.