In
1995, Pressley took over for the retired
Harry Gant in the No. 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 ran just ten races for Diamond Ridge in
1997, including the
Daytona 500, in which his car flipped on its nose acrobatically in the first few laps. Pressley posted a season-best finish of fourteenth, 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 No. 47 Chevrolet for
ST Motorsports, and finished out the year with three top tens. Over in Cup, he joined the No. 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. Robert Pressley, although competitive in some races, struggled with consistency, and would part ways with Jasper at the conclusion of the 2001 season. In 2002, Pressley had a one race deal with
Melling Racing for the Daytona 500 and locked himself in by qualifying speed on Pole Day, Qualifying fifth overall with the same car they had qualified third or better on the 2001 restrictor plate tracks. After receiving sponsorship from Brand Source, he had an engine problem at the end of the race. When he blew up, his car was nearly destroyed on pit road as an accident happened on the tri-oval and
Michael Waltrip's car came across onto pit road, also nearly hitting the pace car as well. ==Recent years==