Waldmann established himself as one of the leading 250cc riders of the mid-to-late 1990s. In 1996 he finished second in the world championship to Biaggi. The following year, 1997, he mounted an even stronger challenge, winning four races and trailing Biaggi by only two points at the season's end — one of the closest 250cc title races of the decade.
After his near-miss in 1997, Kenny Roberts offered Waldmann a 500cc ride for 1998 on a Modenas-powered machine. The step up to the premier class proved difficult; the machinery was uncompetitive and Waldmann finished fourteenth in the championship. He returned to the 250cc class in 1999, joining the Aprilia factory squad and resuming the front-running pace that had defined his earlier seasons.
Waldmann's most celebrated moment came at the British Grand Prix at Donington Park in 2000. Running on wet tyres on a track that was drying rapidly, he fell over a minute and a half behind the leaders with ten laps remaining and appeared set for a distant finish. When rain returned to the circuit, his choice of tyres became advantageous and he mounted a remarkable charge from what amounted to nearly a lap in arrears. He crossed the line to win by just 0.3 seconds from Frenchman Olivier Jacque at the final corner — an extraordinary reversal that remains one of the most remarkable victories in 250cc history.
Waldmann retired from racing competition after the 2002 season. In 2003 he signed with the new Harris WCM MotoGP team for what would have been a return to the premier class, but he left the programme before the season began, unable to adapt to the new generation of four-stroke Grand Prix machinery.
In 2009, Waldmann joined Martin Wimmer in acquiring the German motorcycle manufacturer MZ from the Hong Leong Group, demonstrating a continued connection to the motorcycle industry beyond his racing career. That same year he also briefly returned to Grand Prix competition, substituting for the injured Vladimir Leonov at the British Grand Prix.
Waldmann died on 10 March 2018 in Ennepetal, Germany, of a suspected heart attack. He was 51 years old.
Ralf Waldmann's career was defined by his intense rivalry with Max Biaggi in the 250cc class. His 1996 and 1997 championship runner-up finishes came in seasons when Biaggi was at the peak of his powers, and the margins that separated them — particularly the two-point deficit in 1997 — illustrate how closely matched the two were. His extraordinary victory at Donington Park in 2000 stands as the enduring highlight of a career that placed him among the most capable 250cc specialists of his generation.