On July 29, 1903, Dougherty became the second Red Sox player (then known as the Americans) to hit for the cycle.[1] 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,[2] 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).
In a 10-year major league career, covering 1233 games, Dougherty compiled a .284 batting average (1294-for-4558) with 678 runs, 17 home runs, 413 RBI and 261 stolen bases. In his two postseason appearances, in the 1903 and '06 World Series, he batted .185 (10-for-54) with 2 home runs and 6 RBI.
Dougherty died in Bolivar, New York, at the age of 63 and was buried at St. Mary Catholic Cemetery in Bolivar.[3]