His first major competition was the 1999 IAAF World Cross Country Championships and he finished in fifth place in the long race and helped secure a dominant Kenyan finish in the team competition. Rutto became an elite runner at the 10k to half marathon distances: he won the 2001 Beach to Beacon race and was the top Kenyan finisher at the 2001 IAAF World Half Marathon Championships with a run of 1:00:43 for sixth place.