In 1994, Kevin Windham started his career on a privateer Kawasaki KX125. For the 1995 season, Kevin got picked up by factory Yamaha to ride their YZ125. Kevin won two West coast Supercross titles for Yamaha in 1996 and 1997 on the YZ125. In 1998 he stepped up full-time to the 250 class staying with team Yamaha finishing 4th in Supercross and 8th in the outdoor series. In 1999, Kevin switched manufactures to factory Honda to ride their CR250. That year he won two Supercross races and four outdoor Nationals. Then in 2001 he made another switch to factory Suzuki. In an eight year span, Kevin had rode every major manufacture brand, the big four (Kawasaki, Yamaha, Honda, Suzuki). He only raced the RM250 for one and a half seasons. He won two outdoor Nationals for them until switching back to Honda.
That year in 2001 on his RM250 Kevin finished second in points behind Ricky Carmichael and forth in points in Supercross behind Ricky Carmichael, Jeremy McGrath and Mike LaRocco. He was also picked to race the Motocross Des Nations that year, but that fateful day of 9/11 struck and USA pulled out of the race. The team that never got to race was Ricky Carmichael, Kevin and Mike Brown.