Bennett made five starts in 1999, all for ReyBen Racing. Bennett's debut came at Martinsville, where he qualified 25th but fell out due to engine problems. He finished that race 31st. Bennett improved signifcantly after that, finishing in the top-20 in three of four races. He had two 19th place finishes (at Nazareth and Richmond) as well as a 20th at Watkins Glen. The Glen, where Bennett started 20th, was his best qualifying effort en route to a 41st in points.
Bennett returned for five more races in 2000, once again having a respectable season. At Homestead-Miami, Bennett set a career best start of 14th and finish of the same position. Other good finishes included a 15th at Loudon and 21st at Dover. Bennett did not finish the other two starts due to mechanical issues.