In 2003, Wood notched two poles, 10 top fives and 20 top ten finishes, including two wins on his way to a fifth-place standing in points. He ran most of the season with sponsored by Bob Graham. He ran his second Busch race that season at the Ford 300 in the #15 for ppc Racing. He finished 22nd. Unfortunately, the 2004Craftsman Truck Series season was a struggle for Wood, who was forced to run unsponsored for virtually the entire season. As a result, Roush Racing focused more on teammate Carl Edwards, and he had a pair of top fives and a fifteenth-place point result.
Wood moved to NASCAR's Busch Series full-time in 2005, driving for ST Motorsports (which later merged with the Wood Brothers to form Wood Brothers/JTG in 2006.) Wood had two top-fives and finished fifteenth in points, finishing fourth in the Rookie of the Year standings. In August 2005, Wood was released from his development contract with Roush Racing, and became a member of the Wood Brothers driver development program. Wood had one top-five finish in 2006 and moved up one spot in the standings.
Originally, plans called for Wood to move up to Nextel Cup full-time in 2007; however, because of sponsor issues and the need for more experience, Wood ran only a partial schedule during the 2007 Nextel Cup season. Wood was to continue to drive full-time in the #47 Clorox-sponsored Ford Fusion in the Busch Series, but was pulled from the ride following medical issues. He spent the rest of the season back in the Truck Series in the #21 Ford and had six top-tens in eleven starts as well as a pole position. He shared the #21 truck in 2008 with his cousin Keven but only had two top-ten finishes. He also made three Sprint Cup starts that season but failed to finish higher than 33rd. At the end of the season, the Woods' truck team closed down and he has not raced since.