Following his father, Graziano Rossi, Rossi started racing in Grand Prix in 1996 for Aprilia in the 125cc category and won his first World Championship the following year. From there, he moved up to the 250cc category with Aprilia and won the 250cc World Championship in 1999. He won the 500cc World Championship with Honda in 2001, the MotoGP World Championships (also with Honda) in 2002 and 2003, and continued his streak of back-to-back championships by winning the 2004 and 2005 titles after leaving Honda to join Yamaha, before regaining the title in 2008 and retaining it in 2009. He left Yamaha to join Ducati for the 2011 season.
Rossi is first in all time 500 cc/MotoGP race wins standings, with 79 victories, and second in all time overall wins standings with 105 race wins (behind Giacomo Agostini with 122).
Rossi won the regional kart championship in 1990. After this he took up minimoto and before the end of 1991 had won numerous regional races.Rossi continued to race karts and finished fifth at the national kart championships in Parma. Both Valentino and Graziano had started looking at moving into the Italian 100cc series, as well as the corresponding European series, which most likely would have pushed him into the direction of Formula One. However, the high cost of racing karts led to the decision to race minimoto exclusively. Through 1992 and 1993, Valentino continued to learn the ins and outs of minimoto racing.
In 1993, with help from his father, Virginio Ferrari, Claudio Castiglioni and Claudio Lusuardi (who ran the official Cagiva Sport Production team), he rode a Cagiva Mito 125cc motorcycle, which he damaged in a first-corner crash no more than a hundred metres from the pit lane.He finished ninth that race weekend.Although his first season in the Italian Sport Production Championship was varied, he achieved a pole position in the season's final race at Misano, where he would ultimately finish on the podium. By the second year, Rossi had been provided with a factory Mito by Lusuardi and won the Italian title.
Rossi had some success in the 1996 World Championship season, failing to finish five of the season's races and crashing several times. Despite this, in August he won his first World Championship Grand Prix at Brno in the Czech Republic on an AGV Aprilia RS125R. He finished the season in ninth position and proceeded to dominate the 125cc World Championship in the following 1997 season, winning 11 of the 15 races.
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