Schilling began his career with the Baltimore Orioles (1988-1990), spent one year with the Houston Astros (1991), and then spent the bulk of it with the Philadelphia Phillies (1992-2000). He was traded mid-season to the Diamondbacks in 2000. With Arizona, he went 22-6 with a 2.98 ERA in 2001 and went 4-0 with a 1.12 ERA in the playoffs. In 2002, he went 23-7 with a 3.23 ERA. Both years he finished second in the Cy Young Award voting to teammate Randy Johnson.