In 1999, Windham won the United States Grand Prix of Motocross held at Budd's Creek, Maryland.

[3] Regarded as one of the most naturally talented riders competing in motocross and supercross, Windham has finished second in the overall points standings five times, without once winning.

[3] Though one of the oldest riders on the track in 2011, his acknowledged class, grace, and riding ability make him a favourite with the fans.

He also had some strong performances in the outdoor nationals with a top 125cc Motocross finish of fifth at Delmont, PA.[3] 1996 was a breakthrough year for Windham, with six supercross wins he scored his first 125cc West Coast Championship.

He took podium finishes in the 250cc Motocross National races at Budds Creek, MD, and New Berlin, NY, but failed to score an overall victory.

In the 1999 season, after some initial struggles adapting to his new bike, Windham hit his stride and won two Supercross main events and four motocross Nationals.

Windham and Sebastien Tortelli both posed strong challenges to Albertyn all season, but eventually came up short.

The same year, Windham decided to race the USGP being held at Budd's Creek, MD only a few days prior to the event.

In 2002, he began the season for Team Sobe Suzuki with a broken finger, and had difficulty adjusting to the race situation with crowds and lights.

Windham did not return to the circuit that season and many speculated that he would retire at the young age of 23, however the rest allowed him to fully recover mentally and physically.

With an emphasis on having fun and just enjoying the sport, Windham rode better than ever before, claiming two overall victories at Unadilla and Washougal, and finishing on the podium at all but two events.

Carmichael had switched to a partial schedule, and Windham was beaten by eventual champion Stewart, Reed and Tim Ferry.

He held the fastest qualifying times at a number of events including Atlanta, Georgia and Jacksonville, Florida.

He rode the first half of the 450 Class Motocross Championship, filling in for injured Honda riders Trey Canard and Josh Grant, achieving a number of top-10 finishes.

[14] He volunteered to join GEICO Honda teammates Justin Barcia and Eli Tomac to replace Christophe Pourcel, injured two weeks before, at the 29th annual Supercross of Bercy at Omnisport Paris, however he was unable to finalize travel documents in time.

[15] In 2012 Windham continues with Geico Powersports Honda, entering his 19th season as a professional motocross racer.

However, while battling with James Stewart Jr. on the Final Lap during Heat of Round 13 at Houston, Windham crashed hard and suffered several injuries.

Born in Baton Rouge, Louisiana, Windham began riding motorcycles from the age of three with friends in the spillways around the New Orleans area.

[19] The couple have four children; daughters Madelyn, Annabelle and Elizabeth, and son Kevin Jr. Windham lists his non-motocross hobbies as "anything outdoors", including bmx, fishing and flying his own plane.