Pudge Heffelfinger, the legendary All-American from Yale University, gave this description of Osgood: "It was downright uncanny to watch him run, opponents missed him by inches.

He ran the 440 and put the shot for the track team, was an accomplished gymnast, boxer, wrestler, tennis player, and set a collegiate record of 5:28 for the 2-mile bicycle race.

At Pennsylvania, Osgood continued his exploits as a three-sport athlete, excelling at football, track and field, and wrestling.

He lettered two seasons at halfback for the Quakers under Hall of Fame coach George Washington Woodruff.

Osgood received widespread press in the 14–6 loss to Yale, as he scored Penn’s only touchdown in the game.

The 1894 squad featured one of the greatest backfields of all time, consisting of Carl Sheldon Williams at quarterback, George Brooke at fullback, and Osgood and Alden Knipe at halfback.

he would lead them to a record of 5–2, with an impressive win 18–0 over an undefeated Notre Dame and a 28-0 blank of Butler University on Thanksgiving.

After much hard fighting and a brilliant charge led by Colonel Mario García Menocal, the largest fortification was taken.

When Osgood stooped over the gun to adjust the sight to account for the wind, he made the remark, “think that will do.” At that moment, he was hit by a bullet fired by a sharp-shooter stationed in the church tower eleven hundred yards away.

Without re-sighting the artillery piece, Osgood’s second in command Major Frederick Funston gave the order to fire the gun and the shell hit one of the blockhouses.