He received a no-decision, going 5 innings, allowing one run, and striking out 4. On April 6, Tillman earned his first win of 2014, going 8 innings against the Detroit Tigers, allowing one run and striking out 5. On May 17, Tillman pitched his first career complete-game shutout, against the Kansas City Royals. Tillman made his first career postseason start during Game 1 of the American League Division Series, against the Detroit Tigers. He was the winning pitcher, going 5 innings, allowing 2 runs, and striking out 6, as the Orioles defeated the Tigers 12–3. The Orioles would eventually get swept in the 2014 American League Championship Series. Tillman finished the season with a career-high 34 starts, 207 innings pitched, and a 13–6 record. His 15 no decisions were the most among MLB starting pitchers in 2014. He recorded a 3.34 ERA and 1.23 WHIP while striking out 150 batters.