1921

New Jersey plumber Frank Zuna smashed the course record of 1912 winner Mike Ryan with a powerful 2:18:57 performance, upsetting defending champion Peter Trivoulidas, who finished third. Zuna and eventual second-place finisher Chuck Mellor, formed a two-member lead pack through 16 miles. However, Zuna took off on the first of the Newton Hills, and ran uncontested to the finish.

1922

This was the second of Clarence DeMar's victories. It was also the beginning of the DeMar era which saw the Melrose printer and church volunteer score a string of five additional triumphs during the ensuing eight years, including three consecutive victories beginning this year. At age 33, DeMar established a permanent record (2:18:10) for the 24.5 mile course, which was abandoned two years later in favor of the standard 26-mile, 385-yard Olympic distance. Medford's Jimmy Henigan battled DeMar from mile seven through 20, but DeMar was able to pull away on the downgrade past Boston College, where Henigan dropped out.

1923

This was the second of DeMar's three consecutive wins (2:23:37) and the last race at the 24.5 mile distance. After taking the lead from Whitey Michelson at Cleveland Circle, DeMar held off the late challenge of 1921 winner Frank Zuna. Willie Carlson of Chicago closed fast over the latter stages of the race to finish third, ahead of the fading Michelson.

1924

DeMar completed a three-year sweep with a 2:29:40 performance. The race course was lengthened to what was thought to be 26 miles, 385 yards, in order to comply with the standard Olympic marathon distance. However, upon remeasurement in 1927, the course was found to be 197 yards short of the official distance. DeMar was strong throughout his 1924 effort, defeating runner-up Chuck Mellor of Illinois by more than five minutes.

1925

Chuck Mellor of Chicago succeeded in his fifth Boston attempt, winning the race in 2:33:00 and spoiling DeMar's bid for a fourth consecutive title. Running with a wad of tobacco tucked inside his cheek and the morning edition of the Boston Globe placed inside the front of his shirt to serve as a windbreaker, Mellor finally pulled away from DeMar on Beacon Street, within two miles of the finish.