Dermody attended Norwalk High School in his hometown of Norwalk, Iowa. In his senior season, he pitched to a 10–3 win–loss record, 1.26 earned run average (ERA), and 164 strikeouts. He also recorded the first six-inning, 18 strikeout perfect game in Iowa state history. In addition, Dermody hit .434 with 51 runs batted in (RBI). His pitching performance that year earned him the Bob Feller Pitching Award. Dermody was selected by the Pittsburgh Pirates in the 26th round of the 2009 Major League Baseball draft, but did not sign and instead attended the University of Iowa. With the Hawkeyes in 2010, Dermody made 10 appearances, seven of which were starts, and posted a 7.93 ERA. The following season he made 14 starts and went 4–6 with a 4.15 ERA and 75 strikeouts in 84​2⁄3 innings pitched. The Colorado Rockies drafted Dermody in the 29th round of the 2011 Major League Baseball draft, but he did not sign.\n', '

In 2012, Dermody won Iowa\'s Big Ten Sportsmanship Award, and pitched to a 1–7 record, 4.50 ERA, and 60 strikeouts in 76 innings. He was drafted for a third time, this time by the Arizona Diamondbacks in the 23rd round of the 2012 Major League Baseball draft. Dermody declared his intention to sign with the Diamondbacks, and went to Arizona for a physical examination. The Diamondbacks organization determined that he had a 40 percent tear of the left ulnar collateral ligament, and fearing the injury would require Tommy John surgery, declined to offer him a contract. Dermody then returned to the Hawkeyes for his senior year, making 14 starts in 2013. He had the best season of his college career, posting a 7–2 win–loss record, 3.64 ERA, and 68 strikeouts in 94 total innings.\n', '

The Toronto Blue Jays selected Dermody in the 28th round of the 2013 Major League Baseball draft, and he signed on June 14. He was assigned to the Rookie-level Gulf Coast League Blue Jays, where he made one scoreless relief appearance before being promoted to the Short Season-A Vancouver Canadians of the Northwest League. In 43​1⁄3 total innings that season, Dermody posed a 5–1 record, 1.66 ERA, and 51 strikeouts. In 2014, Dermody was promoted to the Class-A Lansing Lugnuts, where he pitched to a 4–6 record, 4.69 ERA, and 65 strikeouts in a career-high 96 innings. Dermody was assigned to the Advanced-A Dunedin Blue Jays for the 2015 season. In 77 total innings that season, he was 4–1 with a 4.21 ERA and 62 strikeouts.\n', '

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