On July 29, 1903, Dougherty became the second Red Sox player (then known as the Americans) to hit for the cycle. In Game 2 of the 1903 World Series, the first modern World Series, Dougherty became the first player to accomplish several feats; he became the first Boston player to hit a World Series home run, the first player to hit two home runs in a single World Series game, and the first player to hit a leadoff inside-the-park home run in a World Series game (a feat not matched until the 2015 World Series, by Alcides Escobar of the Kansas City Royals in Game 1).