A graduate of St. Mary's High School in Manhasset, New York (1955) and Manhattan College (1959),[1] he threw and batted right-handed, stood 5 feet 11 inches (1.80 m) tall and weighed 170 pounds (77 kg).

After playing for Boston's Triple-A Minneapolis Millers farm team in 1960, Schilling broke into the Major Leagues in 1961, the same year as his friend and fellow Long Islander, eventual Hall of Famer Carl Yastrzemski.

A slick fielder, his arrival prompted the Red Sox to move the incumbent American League batting champion, Pete Runnels, from second base to first baseman and utility infielder.

He won the Red Sox' Most Valuable Player (now the Thomas A. Yawkey) Award for 1961 as bestowed by the Boston chapter of the Baseball Writers' Association of America.

[2] In 1962, Schilling's sophomore season, he suffered a broken hand, causing him to miss over 40 games and impairing his batting ability for the rest of his career.