In 1957, Drabowsky was the Cubs' number two starter. He was 4–8 with a 5.04 ERA through July 4; after that, he went 9–7 the rest of the way, with a 2.51 ERA. Control problems affected him during the year, such as in a game against the Cincinnati Redlegs on June 2, when he hit four batters (including future teammate and Hall of Famer Frank Robinson twice) in innings, tying a major league record. On August 4, in the first game of a doubleheader against the Pittsburgh Pirates, Drabowsky threw a shutout in a 6–0 victory. He threw another shutout against Cincinnati on September 4, also in the first game of a doubleheader, giving up just two hits this time in a 1–0 victory. Drabowsky finished the year with a 13–15 record. His 170 strikeouts tied him for second in the National League with teammate Dick Drott, behind another rookie, Jack Sanford of the Philadelphia Phillies, who had 188. His 33 games started were 4th (tied with Lew Burdette and Sanford), 239 innings pitched 6th, and 12 complete games 8th in the NL (tied with Brooks Lawrence and Don Newcombe). Additionally, he led the league with ten hit by pitches.