Stephenson had another breakout season in 2013–14, posting career highs across the board in his second year in a starting role. On November 11, 2013, he scored 13 points with career highs of 12 assists and 11 rebounds for his first career triple-double as the Pacers defeated the Memphis Grizzlies 95–79. He had his second career triple-double eleven days later, recording 10 points, 10 assists and 11 rebounds in a 97–82 win over the Boston Celtics. On December 22, 2013, he recorded his third career triple-double with 12 points, 10 rebounds and 10 assists in a 106–79 win over the Celtics. On January 16, 2014, Stephenson scored a career-high 28 points in a 117–89 win over the Knicks. He finished the regular season with a league-high five triple-doubles, and finished second in NBA Most Improved Player Award voting. The Pacers entered the playoffs as the first seed in the Eastern Conference and advanced to the conference finals, where they lost to the Miami Heat for the second straight year. His unusual tactics made headlines during the Eastern Conference finals against the Miami Heat, including blowing in the ear of LeBron James during a game five win.