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 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.