Over the next five years, Jurek notched victories in the McDonald Forest 50K (1999), the Bull Run Run 50 Mile (1999), the (2000, 2001, 2002, 2004), the Diez Vista 50K (2000-course record, 2003), the Silvertip 50K (2002), and the Miwok 100K (2002, 2003, 2004). In 2004, he completed the "Ultra Running Grand Slam" by finishing Western States, the Leadville 100 (in which he was runner-up), the Vermont 100, and the Wasatch Front 100. He traveled to Hong Kong with Team Montrail to win the 2001 and 2002 Oxfam Trailwalker 100K team trophies, both years setting new course records. Jurek's 2001 teammates were Dave Terry, Ian Torrence, and Nate McDowell. In 2002, he ran with McDowell, Brandon Sybrowsky, and Karl Meltzer. Jurek was also on the winning team of the 2003 Hasegawa Cup Japan Mountain Endurance Run.