1926

A 20-year old delivery boy, John C. Miles of Sydney Mines, Nova Scotia, upset Olympic champion Albin Stenroos of Finland and course record holder DeMar. Miles ran in dogged pursuit of the Olympic champion, finally catching up with the gold medalist at Boston College, where Stenroos was slowed by a side stitch. Miles slashed four minutes from DeMar's 1924 record with a stunning 2:25:40 performance.

1927

Although the course was lengthened to the full marathon distance of 26 miles, 385 yards, the finish was familiar as DeMar claimed his fifth title in 2:40:22. Just shy of his 39th birthday and running in 82-degree heat, DeMar led at every checkpoint en route to winning the race which served as the AAU title this year.

1928

Aggressive racing by DeMar once again resulted in back-to-back victories and his sixth win as the field grew to 254 runners. DeMar took over in Natick, 10 miles into the race, with Philadelphia's Bill Wilson nagging at his heels until 18.5 miles. DeMar slowly pulled away, and crossed the line in 2:38:07, while celebrated miler Joey Ray finished third.

1929

John C. Miles, the 1926 champion, returned with a course record performance of 2:33:08. The 23-year-old Miles, who had been forced to drop out at five miles in 1927 and didn't run in 1928, waged a tough battle with Whitey Michelson from miles 13 through 23 before pulling away on Beacon Street. Finnish runners Karl Koski and Willie Kyronen closed fast to catch Michelson in the final miles.

1930

DeMar chalked up his seventh and final victory in 2:34:48 on a hot and humid afternoon. At age 41, DeMar became the oldest runner ever to win Boston. After following pace-setter Hans Oldag of Buffalo for 16 miles, DeMar began to pull away on the Newton Hills at record pace. He slowed in the final miles, thereby losing his bid for a course record, but easily finished ahead of runner-up Willie Kyronen.