Once in Baltimore, Drabowsky was used almost exclusively as a relief pitcher. After three starts in 1966, he would pitch only in relief the rest of his career. He became a part of one of the best bullpens in the major leagues and posted ERAs of 2.80, 1.60, and 1.91 during his first three years with the club. The Orioles won the American League (AL) pennant in 1966, and in Game 1 of the World Series, Drabowsky relieved an innefective Dave McNally with the bases loaded and one out in the third inning. Though he walked a batter to let in a run, he finished the inning with the Orioles leading 4–2, and he threw six scoreless innings after it to preserve the Game 1 victory. The Orioles would sweep the Los Angeles Dodgers in four games, making Drabowsky a World Series champion for the first time.