The highlight of his career came in 1983, when the Orioles won the American League Eastern Division pennant, then defeated the Chicago White Sox in the 1983 American League Championship Series, before winning the 1983 World Series against the Philadelphia Phillies. Dempsey posted a .385 batting average along with a .923 slugging percentage in the five-game series, and won the World Series Most Valuable Player Award, one of six catchers to have won the award.