After playing for Boston's AAA 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 a first baseman and utility infielder role. Schilling had a sparkling rookie season, appearing in 158 games and reaching career highs in batting average (.259), hits (167), runs scored (87), and runs batted in (62). He made only 8 errors in 846 chances for a league-best fielding percentage of .991. As a reward, he won 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.
But in Schilling's sophomore season, 1962, he suffered a wrist injury and missed over 40 games, and his batting ability was impaired for the rest of his career. Although he hit a personal-best 7 home runs in 1962, he batted only .230 and he would never again exceed the .240 mark as a hitter. He reclaimed the regular second baseman job in 1963, but batted only .234 in 143 games and lost his regular job to Felix Mantilla and Dalton Jones in 1964.
By the start of the 1966 campaign, Schilling had become a spare part on a poor Red Sox club. Coming out of spring training, he was traded to the Minnesota Twins with catcher Russ Nixon for left-handed pitcher Dick Stigman. Schilling began the season on the Twins' 28-man roster, but he never appeared in any games and retired before the rosters were cut to 25 men on May 15.
During his five season career, Schilling batted .239 in 541 games played, with 23 home runs and 146 runs batted in.
In retirement, Schilling returned to Long Island, where he became a secondary-school mathematics teacher and played competitive softball until the age of 69.