In 1903, Phillippe earned the honor of starting the first World Series game for the Pirates against the Boston Americans in 1903. In a complete game victory, Phillippe struck out 10 batters and earned the win against Cy Young to start the best-of-nine series. He single-handedly guided the Pirates to a 3–1 series lead, earning the wins in each game, but when his arm wore down due to overuse, the Americans came back to win the series 5 games to 3, with Phillippe losing the last two. His five decisions in the World Series are still a record for a pitcher. To show their appreciation, Pirates' fans presented him with a diamond horseshoe stickpin and team owner Barney Dreyfuss rewarded him ten shares of stock in the club.