Vande Velde started his Grand Tour career by participating in the 1998 Vuelta a España, where he assisted Lance Armstrong, to a fourth-place finish. Vande Velde twice rode on the Tour de France team that brought Lance Armstrong to victory, in 1999, and 2001. In the 1999 Tour de France, Vande Velde was for a time the leader of the young rider classification; he did not compete, however, in the 2000 Tour de France. Vande Velde moved to in 2004, and switched to in 2005. During this time, he worked as a domestique, riding in support of varying team captains, even though the 2005 season saw Vande Velde taking chances of his own. In one instance, Vande Velde was a breakaway participant on the fourth stage of the Eneco Tour. The breakaway, however, was eventually hampered when the peloton was led on a false route, meaning the breakaway riders had to wait for the peloton to get back on track, at which time the gap between the break and the peloton was reduced from six to four minutes with 43 kilometres to go.