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Biffle started his racing career in 1990 entering Skip Barber events. In 1993, Biffle finished 4th in the Barber Saab Pro Series. In 1994, Biffle moved to Europe and drove in the Formula Opel Lotus series. In 1995 Biffle finished 9th in British Formula 3. In 1996 Biffle moved back to the USA and gained national attention when he raced in the NASCAR Winter Heat series on ESPN2 in the winter of 1995/1996. Former ESPN announcer and NASCAR champion Benny Parsons told Jack Roush that there was no way he could pass up the chance to hire Biffle, and that if he did he would regret it while watching Biffle win races for another team owner.

Starting in the NASCAR Craftsman Truck Series, Biffle first won Rookie of the Year in 1998 for Roush Fenway Racing. In 2000, he won the series title in the #50 Grainger Ford F-150, which was his first championship in one of NASCAR's three major series. In 2001, he ran four more races for Jack Roush in the #99 Eldon Ford F-150. His last truck start was in 2004 for Tom Mitchell in the #44 Ford Racing Ford F-150 at Homestead-Miami Speedway.

Biffle first drove two races in 1996 for Dick Bown in the #51 Barbasol Chevrolet Monte Carlo. Biffle joined the NASCAR Busch Series full-time in 2001. He won the series rookie of the year award. He had five wins and finished fourth in points. In 2002 Biffle brought Roush another championship, this time in the NASCAR Busch Series. His four wins, 20-top-fives and 25-top-tens earned him the championship victory over fellow Busch Series regulars Jason Keller and Scott Wimmer. Biffle has continued to drive in the Busch Series every season since then. Biffle ran only part-time in 2003, but contended for the NASCAR Busch Series championship again in 2004, finishing third behind future Sprint Cup Series regulars Martin Truex, Jr. and Kyle Busch. Running part-time again in 2005, Biffle again placed in the top ten in NASCAR Busch Series points standings, despite running only 27 races, eight races fewer than the full season.

In 2002, Biffle drove his first NASCAR Winston Cup Series (now Sprint Cup Series) race at California Speedway in the #16 Volvo Trucks Ford Taurus for Roush Fenway Racing. He also drove for Andy Petree Racing in the #55 Schneider Electric Chevrolet Monte Carlo and for Petty Enterprises in the #44 Georgia Pacific Dodge Intrepid. In total, Biffle ran seven races with three-top-five starts and a best finish of 13th.

Biffle started competing full time in NASCAR's top circuit in 2003, and he finished

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