1897

John J. McDermott, representing the Pastime Athletic Club of New York City, captured the first running of the Boston Marathon - then known as the B.A.A. Road Race. Fifteen runners started the first race with 10 finishing the 24.5 mile trek from Metcalf's Mill in Ashland, Mass., to the finish line at the Oval on Irvington Street, in downtown Boston. McDermott, who had won the only other marathon on U.S. soil the previous October in New York, took the lead from Harvard athlete Dick Grant over the hills in Newton. Although McDermott walked several times during the final miles, he still won by a comfortable six-minute, fifty-two-second margin in 2:55:10.

1898

The second running of the B.A.A.'s Road Race attracted 25 starters and witnessed 15 runners successfully complete the distance. Canadian Ronald MacDonald, a 22-year-old Boston College student, who donned bicycle shoes for his first marathon attempt, overhauled New York cross-country champion Hamilton Gray with just over two miles remaining, before crossing the line in a triumphant 2:42. His time was considered a world-best performance for the marathon at the time. Defending champion John J. McDermott was fourth (in 2:54:17), while pre-race favorite Louis Liebgold of Gotham, New Jersey, wearing bib No. 1, was forced to drop out of the race.

1899

At 173 pounds, Cambridge blacksmith Lawrence Brignolia is the heaviest runner ever to win the Boston Marathon. Brignolia, who seemed quite suited to tackle the strong gale-like winds that hampered runners the entire way, caught Harvard alumnus Dick Grant on the Newton hills, and finished in 2:54:38. The strength of the winds reportedly caused Brignolia to step on a loose stone and fall during his approach to Kenmore Square. Stopping to regain his composure, Brignolia walked and ran the remaining distance to the new finish line on Exeter Street, in front of the B.A.A. clubhouse.

1900

Influenced by MacDonald's victory in 1898, Canadian runners began to establish themselves in the marathon. Led by John P. Caffery of Hamilton, Ontario, the Canadian runners finished 1-2-3 as fellow countrymen Bill Sherring and Frank Hughson followed Caffery across the finish line. Caffery finished in 2:39:44 after overtaking Sherring in Auburndale, 16 miles into the race. The race was marked by the only false start in the race's history as Canadian John Barnard "jumped the gun" and the runners had to be reassembled at the start.