The Italian rider is one of the most prolific sprinters in the history of Italian cycling.

He had success in the World Championship Road Race, one-day classics, and Grand Tours.

Cipollini won the World Championship Road Race in 2002 in front of Robbie McKewen of Australia and Erik Zabel of Germany.

Cipollini won the Points Jersey three times in the Giro d'Italia, in 1992, 1997, 2002.

In addition, Cipollini won the Milan-San Remo Classic in 2002.

Known as the "Lion King" or "Super Mario", Cipollini competed in all three Grand Tours. He would win stages and wear the overall and/or points jerseys during the first week then retire from the race before the high mountains.

He won 191 races in his career including 42 stages, the all-time record in the Giro d’Italia.