Chiappucci placed third in the 1991 Tour de France behind Miguel Indurain and Gianni Bugno of Italy.
Chiappucci also won the Mountains Jersey in the Tour twice, in 1991 and 1992.
In the Giro d’Italia, Chiappucchi placed second in 1991 to Franco Chioccioli of Italy.
Chiappucci also placed 2nd to Miguel Indurain in 1992, and placed 3rd in 1993 behind Miguel Indurain and Piotr Ugromov of Latvia.
In addition, Chiappucchi won the Mountains Jersey three times, in 1990, 1992, and 1993. He also won the points jersey in 1991.
In the one-day events, Chiappucchi was second to Luc Leblanc of France in the 1994 World Championship Road Race.
Chiappucchi also won the 1991 Milan-San Remo Classic and the 1993 San Sebastian Classic.