as an amateur, he finished second in the 1995 junior world championships and his first big result was winning the u-23 world championships in 1998. in his youth he fiercely competed with fellow italian riders giuliano figueras and especially danilo di luca who proclaimed he would have won the u-23 world championship himself had it not been for the team tactics. before basso could turn professional, his parents wanted to see him finish his technical geometry studies. he turned professional with davide boifava's riso scotti-vinavil team in 1999, where he rode his first giro d'italia. he did not finish the three-week race, but he made it a priority to win it some day. in 2000, with the team now called amica chips-tacconi sport, he won his first professional victories in the 2000 regio-tour.