[1][2] He graduated from The English High School in 1872 and upset his family by rejecting an opportunity to attend Harvard College in order to become an actor.

[4] He analyzed football as if it were a battlefield and devised plays based on his study of Napoleon Bonaparte and military tactics.

He worked with the Harvard team on a voluntary basis to perfect the flying wedge, a violent assault by several men on a single opponent.

[6] Harvard's 1892 team had an undefeated 10-0 record heading into its end-of-year showdown with the Yale Bulldogs, coached by football pioneer Walter Camp.

Against Yale in 1892, Harvard opened the second half with a kickoff, but in those days it was legal to tap the ball and then put it in play by running with it or handing or pitching to a teammate.

According to football historian Parke H. Davis: Deland divided Harvard's players into two groups of five men each at opposite sidelines.

After amassing twenty yards at full velocity, the "flyers" fused at mid-field, forming a massive human arrow.

Now both sides of the flying wedge pierced ahead at breakneck speed, attacking Yale's front line with great momentum.

[12] Deland led the team to a 4–0 win over the Michigan Wolverines, a 0–0 tie with the Boston Athletic Association, and a 17–14 loss to Penn, the closest game the undefeated Quakers played all year.

[13] Deland and Yale coach Walter Camp collaborated in 1896 to write their comprehensive study of the sport, titled simply Football.