1916

Local boy Arthur Roth of Roxbury, ran a triumphant 2:27:16 to become the first Boston resident to win the race. The 23-year-old draftsman broke from the field at 10 miles and built a three-minute, seventeen-second lead as the runners headed into the Newton hills at 17 miles. Runner-up Willie Kyronen of Finland put on a late burst over the final six miles, but was still 42 seconds shy at the finish. Completely exhausted, Roth collapsed as he breasted the tape and had to be assisted from the finish area by race officials.

1917

New York bricklayer Bill Kennedy stunned a highly-competitive field that included Finnish favorites Hannes Holehmainen and Willie Kyronen. The oldest winner of the race to date at age 35, Kennedy overtook the Finns at the halfway juncture in Wellesley. He withstood a brief challenge from Hans Schuster at Newton Lower Falls, before claiming victory in 2:28:37 over runner-up Sidney Hatch. The race marked the reappearance of Clarence DeMar, who ran for the first time since his victory in the 1911 race. Employing a quick finish over the latter stages of the race, DeMar placed third in 2:31:05.

1918

Due to American involvement in World War I, the traditional Patriots' Day race underwent a change of format. A 10-man military relay race was contested on the course, and the team from Camp Devens in Ayer, Massachusetts bested the field in 2:24:53.

1919

Another local runner took home top honors as the race returned to its traditional format following the War. Quincy's Carl Linder, the New England javelin and decathlon champion, who had been rejected for military service because of flat feet, was victorious in 2:29:13. With less than 2.5 miles remaining, Linder passed Chicago's Frank Gillespie, who had led from the Natick checkpoint. Gillespie, his feet a mass of blisters and blood from his new racing shoes, could not respond to Linder's challenge. Runner-up Willie Wick, at 4 feet, 10.5 inches, was the smallest ever to finish the Boston course.

1920

Greek National Peter Trivoulidas, a New York busboy, was running in eighth place, three minutes behind leader Jimmy Henigan, as he entered the Newton hills. Meanwhile, 1916 winner Arthur Roth of Roxbury overtook Henigan, who was beset with cramps and eventually withdrew from the race. Roth again tried to steal the race by building up a large lead. But as he again began to wobble near Kenmore Square, Trivoulidas surged and easily overtook Roth to win in 2:29:13.