Which driver has the longest span between first and last Indianapolis 500 wins, at 20 years?

Hélio Castroneves has the longest span between his first and last Indianapolis 500 victories, stretching 20 years from 2001 to 2021. He won his first race at Indianapolis in his rookie season and captured his fourth victory two decades later.

Castroneves’s first win came in 2001, when he drove for Team Penske and famously climbed the catchfence after taking the checkered flag. He won again in 2002 and 2009, then returned to victory lane in 2021 with Meyer Shank Racing. That fourth victory made him the fourth driver to win the race four times.

The record is easy to confuse with other Indy milestones. Juan Pablo Montoya has a 15-year gap between his 2000 and 2015 victories, while A. J. Foyt and Al Unser also share the four-win record. Castroneves’s distinction concerns the span from a driver’s first Indianapolis 500 win to his last, not simply the interval between two consecutive victories.