Following his abbreviated Cup run in 1997, Pressley returned full-time in 1998 with the Jasper team, where he posted a then career-best third-place finish at Texas Motor Speedway. Despite being replaced temporarily by Hut Stricklin due to injuries, Pressley finished 32nd in points that year. 1999 was a struggle however, as Pressley and company failed to qualify six times that season, and often had trouble finishing races. Following the addition of Ryan Pemberton in 2000, Pressley was able to increase his position in points to 25th. In 2001, he had five top-tens, nearly won the inaugural Tropicana 400 before finishing in second, and finished 25th in points handing the driving duties to the car for the road course events to Boris Said. Robert Pressley, although competitive in some races, struggled with consistency, and would part ways with Jasper at the conclusion of the 2001 season.