During the month-long period following Tanaka's posting, teams reported to be serious suitors included the New York Yankees, Los Angeles Dodgers, Chicago Cubs, Chicago White Sox, Arizona Diamondbacks, and Houston Astros. On January 22, 2014, Tanaka signed a seven-year contract worth $155 million with the Yankees. The contract contained an opt-out clause after the fourth year and a full no-trade clause.
Tanaka made his Major League debut on April 4, 2014, against the Toronto Blue Jays and gave up a home run to the first batter he faced, ex-Yankee Melky Cabrera. Tanaka would receive his first MLB win in the game, pitching seven innings with eight strikeouts in the Yankees 7–3 win against the Blue Jays. Tanaka made his first Yankees home start on April 9, against the Baltimore Orioles where he struck out ten batters in seven innings but received a no-decision as the Yankees lost the game 4–5. During an interleague game against the New York Mets on May 14, Tanaka recorded his first major league hit off of José Valverde and pitched his first complete game in the majors as the Yankees shut out the Mets 4–0. Tanaka began his American career with a 6–0 record before he received his first loss in the MLB on May 20, as the Yankees lost to the Chicago Cubs 6–1; it was his first loss in any professional baseball league since August 19, 2012.
Following a loss to the Cleveland Indians on July 8, 2014, in which he gave up five runs in 6 ⁄3 innings, Tanaka began to experience discomfort in his right arm. The next day, Tanaka was placed on the disabled list due to right elbow inflammation. He had compiled a 12–4 record with a 2.51 ERA in 18 starts and was forced to withdraw from the All-Star Game as a result of the injury. An MRI revealed that his elbow had a partially torn UCL. At the behest of several doctors, Tanaka received a PRP shot from Yankees' head team physician Dr. Christopher Ahmad and rested his elbow for 6 weeks instead of having Tommy John surgery to repair his UCL. Tanaka returned on September 21 against the Blue Jays, receiving his 13th win of the season in the Yankees' 5–2 victory over the Blue Jays. He would only pitch one more time during the 2014 season, a loss to the Boston Red Sox in which he gave up seven runs (five earned) in 1 ⁄3 innings. In the 20 starts of his first major league season in 2014, Tanaka posted a 2.77 ERA with 141 strikeouts in 136⅓ innings and a 13–5 record.
After his 2014 season, there was much speculation by sports media and fans that Tanaka should have undergone surgery rather than follow his doctors' suggestions and rehab the injury. This was mostly due to the belief that he would need to get the surgery despite the rehab program.