Cadalora began his Grand Prix career in 1984 riding an MBA in the 125cc world championship. His talent quickly earned him a place with the Garelli factory racing team, and in 1986 he won the 125cc World Championship. The title attracted attention from the higher classes, and Giacomo Agostini's Marlboro Yamaha factory team promoted him to the 250cc class.
After several seasons in the 250cc class building experience, Cadalora switched to the Rothmans Honda factory team for 1991. Riding an Erv Kanemoto-tuned Honda NSR250, he claimed the 250cc World Championship that year. He successfully defended the title with Honda in 1992, securing his third world championship overall. The Kanemoto tuning operation, renowned for extracting maximum performance from Honda machinery, was a critical element in both title campaigns.
Cadalora stepped up to the premier 500cc division for the 1993 season, joining the Kenny Roberts-managed Yamaha team as Wayne Rainey's teammate. In a competitive era dominated by Mick Doohan, he displayed consistent brilliance in the 500cc class. His highest championship finish came in 1994, when he placed second in the standings behind Doohan.
For 1996, Cadalora reunited with Erv Kanemoto, this time on a Honda NSR500, and despite limited sponsorship managed to finish the season in third place overall — a testament to the strength of the Kanemoto-Honda combination and Cadalora's technical precision.
The 1997 season brought instability. Cadalora signed with the Promotor Racing team for Yamaha, but the Austrian-backed team collapsed financially mid-season. WCM stepped in with Red Bull sponsorship to rescue the operation, and Cadalora finished the year in sixth place.
For 1998, Cadalora found himself without works Yamaha support as WCM lost official backing. He filled in for the injured Jean-Michel Bayle in the Rainey-Yamaha works team for a handful of races, then moved to help develop the new MuZ race bike. He continued with MuZ through 1999 before finishing his career in 2000 with Kenny Roberts' Modenas team.
Cadalora retired with 34 Grand Prix victories across the 125cc, 250cc, and 500cc classes — a record of achievement in three different categories that few riders of his era could match. His ability to adapt from the precise, momentum-dependent 125cc machines to the powerful and physically demanding 500cc bikes demonstrated a breadth of skill that defined his career. His two 250cc titles with the Kanemoto Honda operation remain among the highlights of Aprilia's and Honda's small-class rivalry period, while his second-place finish in the 500cc standings in 1994 marked him as one of the genuine challengers to Doohan's dominance.