As his father, also named Robert, was a short track racer in Asheville, the younger Pressley followed a sports career.

In 1994, he ran three races in the Winston Cup Series in a car sponsored by Manheim Auctions, his best finish being a 31st at Charlotte.

In 1995, Pressley took over for the retired Harry Gant in the #33 car owned by Leo Jackson Motorsports in Cup.

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.

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.

Robert Pressley, although competitive in some races, struggled with consistency, and would part ways with Jasper at the conclusion of the 2001 season.

He signed with Bobby Hamilton Racing and won his Truck Series debut at Daytona International Speedway.

[5] Pressley served as promoter at the Kingsport (TN) Speedway from 2011-2014, moving the track to NASCAR Whelen All-American Series-sanctioned status beginning with his first season.

[6] Pressley also owns a restaurant in the Asheville, North Carolina area called Celebrity's Hot Dogs.