Robert Pressley - Winston Cup

Winston Cup

In 1995, Pressley took over for the retired Harry Gant in the #33 car owned by Leo Jackson Motorsports in Cup. He posted one top-ten finish and was runner-up to Ricky Craven for Rookie of the Year. The following year, he put together two top-five finishes. Unfortunately, Jackson was retiring and sold his operation to crew chief Andy Petree. After Pressley ran just one race for his new owner, he was released, but able to hook onto a ride with Diamond Ridge Motorsports. Pressley just ran ten races for Diamond Ridge in 1997, posting a best finish of 14th, when he was suddenly fired from the ride. While he waited for a Cup ride to appear, Pressley returned to the Busch ranks, running the #47 Ford for ST Motorsports, and finished out the year with three top tens. Over in Cup, he joined the #77 Jasper Motorsports team, which became one of the more popular tandems in the Cup circuit among fans.

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.