With Baltimore, Dwyer became one of Manager Earl Weaver's key platoon players, primarily used as a corner outfielder, designated hitter and pinch-hitter. He enjoyed a good season in , hitting .304 (74-for-260) in 71 games, but his most productive year came in , when he appeared in 100 games while hitting .286 with eight home runs and 38 runs batted in, helping his team to reach the World Series, won by Baltimore in five games. In Game 1 on October 11, 1983, Dwyer became the 18th player to hit a home run in his first World Series at-bat when he homered off John Denny for the Orioles' only run in their 2-1 loss to the Philadelphia Phillies.