Lance Armstrong vs Jan Ullrich

While Jan Ullrich won the Tour de France in 1997, he was never able to beat Lance Armstrong during Armstrong's dominant run from 1999 to 2005. Ullrich finished second to Armstrong multiple times, creating a captivating rivalry centered around the Tour de France. Their competition was defined by dramatic strategic battles in the mountains.

Both cyclists were heavily implicated in widespread doping scandals that ultimately tainted the era of cycling. Armstrong was stripped of all seven of his Tour de France titles and banned for life, while Ullrich was also found guilty of doping and had his results retroactively disqualified. The intense rivalry that dominated the late 1990s and 2000s is now viewed with heavy skepticism.

A famous moment occurred during the 2003 Tour de France when Jan Ullrich crashed on a rainy descent, and Lance Armstrong notably waited for him to catch up out of sportsmanship. Armstrong went on to win that Tour by a razor-thin margin of just 61 seconds over Ullrich. It was the closest Armstrong ever came to losing the Tour during his victorious run.

The American and the German cyclist stood on the final Tour de France podium together three times (1999, 2000, and 2001). In all three of those years, Armstrong took first place, while Ullrich had to settle for second or third. Their head-to-head matchups were the primary draw of the race during that era.