Though Drabowsky was part of the Orioles' roster to begin the 1966 season, he was only used nine times in the team's first 37 games, and he had a 3.94 ERA. At the end of May, he asked pitching coach Harry Breechen if he could throw once every two nights. Pitching more frequently from that time forth, Drabowsky's ERA fell to 2.59 over his final 35 games. Bullpen coach Sherm Lollar speculated joining the Orioles gave Drabowsky new confidence. "We were a contender and could support his pitching." Drabowsky finished the year with six wins, no losses, a 2.81 ERA, and seven saves. He struck out 96 in 98 innings pitched as the Orioles won the American League (AL) pennant, sending Drabowsky to the playoffs for the first time in his career.