Simmons was born in Philadelphia, Pennsylvania on September 27, 1901, according to the National Lacrosse Hall of Fame;[1] The New York Times placed his birth year at 1899 or 1900.

[3] The incident made headlines in the local press, and University of Chicago coach Amos Alonzo Stagg said that he had "too much school spirit.

[8] Post-graduation, he accepted an assistant coaching position for the Syracuse football team; he remained with that program for more than 40 years.

The match was part of an intermittent series of amateur indoor lacrosse games set up in the midst of the Great Depression.

[11] Simmons joined the United States Navy in April 1942, and was an athletic instructor in Georgia until the war ended.

In 1949, the Orangemen were a two-point loss to Army away from going undefeated; their 14 wins were tied for the second-most in program history, equaling the total of the 1925 national championship-winning team.

[12] The next season, the Orangemen featured four players who were named All-Americans, including Simmons's son, Roy Jr.

The squad also featured Jim Brown, who went on to become the National Football League's all-time leading rusher at the time of his retirement.

[15] Simmons had played a role in recruiting Brown to Syracuse; after Brown was refused a football scholarship due to his skin color, Simmons provided money that he had left over for lacrosse recruiting, with other money provided by the track coach.

In recruiting fighters for Syracuse, he traveled to numerous northeastern gyms, and was said to prefer boxers without evident facial damage, as "that proved they knew how to dodge a blow.

He supplemented his rosters with college football players who had finished their senior seasons and had no spring practice sessions.