The 1998 race was run on schedule and had 38 entrants. The 1999 race was won by Alaska Native Ramy Brooks, who defeated veterinarian Mark May by 10 minutes. In 2000, Aliy Zirkle became the first woman to win the Yukon Quest after taking 10 days, 22 hours, and 57 minutes to trek the . Also in 2000, Yukon Quest International added two races: the Quest 250 (today the Quest 300) and the Junior Quest (both described below). Competitors in each have gone on to participate in the Yukon Quest. The first of these graduated mushers competed in the 2001 race, won by Tim Osmar.