When Schilling was young, he was too large to play organized football with kids his own age because Bellevue's youth leagues were regulated by weight-age limits, which caused him to take up basketball instead. Schilling says that his true love was basketball and that he would probably not have experimented with football, but the coach of the basketball team resigned right before his freshman season. During the summer prior to his freshman year, Schilling first visited the Bellevue High School weight room where he noticed the intensity and camaraderie. He eventually became a three-year starter for the football team. As a sophomore, Schilling was part of the Bellevue championship football team whose season extended long enough to interfere with him participating in the early part of the basketball season as a sophomore. The championship, which came as a result of a ten-game winning streak to close the season, made the Bellevue Wolverines three-time Class 3A state champions. On September 4, 2004, as a junior, he helped Bellevue end the high school football record 151-game winning streak by De La Salle High School in front of 24,987 at the second annual Emerald City Kickoff Classic at Qwest Field by a 39–20 score.
