|Dates:||October 7–October 12|
|Umpires:||Tommy Connolly (AL), Hank O'Day (NL), Bill Dinneen (AL), Ernie Quigley (NL)|
|Future Hall of Famers:||Red Sox: Harry Hooper, Herb Pennock (dnp), Babe Ruth. Robins: Wilbert Robinson (mgr.), Rube Marquard, Casey Stengel‡, Zack Wheat.|
‡ elected as a manager.
Casey Stengel shined on offense for the Robins in the 1916 Series but the Red Sox pitching core ultimately proved too much for the denizens of Flatbush. The Sox's Babe Ruth pitched thirteen shutout innings in Game 2, starting a consecutive scoreless innings streak that would reach 29 in 1918. As with the 1915 Series, the Red Sox played their home games at the larger Braves Field, and it paid off as they drew a then-record 42,620 people for the final game.
Brooklyn fielded some strong teams under their manager and namesake Wilbert Robinson in the late 1910s. The Robins, also interchangeably called the Dodgers, would win the pennant again in 1920, but the American League teams were generally stronger during that interval. It would be 39 years before the Dodgers would win their first World Series title in 1955. The series had the longest game in World Series History until Game 3 of the 2005 World Series.
|WP: Ernie Shore (1–0) LP: Rube Marquard (0–1) Sv: Carl Mays (1)
Game 2Monday, October 9, 1916 at Braves Field in Boston, Massachusetts