He made his Winston Cup Series debut, again driving a passed down STP Dodge Magnum numbered No.

Petty took his number and sponsorship to Wood Brothers Racing in 1985,[3] where he had a then career-high seven top-fives and his first top-ten points finish.

The next season, he won his first career race in the infamous 1986 Miller High Life 400 at Richmond and finished tenth in the final standings.

Originally beginning the season unsponsored, he and SABCO later picked up sponsorship from Peak Antifreeze after he drove their car to a top-ten finish at the Daytona 500, filling in for Eddie Bierschwale, as well as Ames Department Stores.

Peak became the team's full-time sponsor in 1990, and Petty finished eleventh in points after winning the GM Goodwrench 500 at North Carolina Speedway with a 26-second margin of victory.

Mello Yello would replace Peak as sponsor of the #42 in 1991, and Petty was running eleventh in points when he suffered a broken leg at a crash in the Winston 500 at Talladega, causing him to miss the next eleven races.

In 1992, Petty rebounded to a career-best fifth-place finish in points, as well winning two separate races that season at Watkins Glen and Rockingham.

He dropped ten spots in points in 1994 after he failed to finish higher than fourth, and lost the Mello Yello sponsorship at the end of the season.

Coors Light became his new sponsor beginning in 1995, and Kyle won his final career Cup race in the Miller Genuine Draft 500 at Dover.

He fell further down to 30th in points after only finishing in the top-ten five times and failing to qualify for the fall race at Bristol Motor Speedway.

In 1996, the popular rock group Soundgarden recorded a song called "Kyle Petty, Son of Richard.

Petty also made guest appearances on ESPN to provide commentary during Busch Series races.

He had one top-ten early in 2000, the same year in which his son Adam died while practicing for a Busch Series race at New Hampshire International Speedway.

44 Hot Wheels Pontiac and qualified in 19 races in 2000, causing him to finish 41st in the points standings in the 2000 Winston Cup Series.

When Georgia Pacific left after 2005, Wells Fargo, Schwan's, and Marathon Oil became the team's new primary sponsors and Petty duplicated his top-ten total in 2006, but fell five spots further in points.

He then raced the Toyota Save Mart 350 at Sonoma in a Petty Enterprises car while broadcasting for TNT.

When the #45 car fell out of the top-35 in owner's points, he took a large portion of the season off, including races that did not conflict with his broadcasting duties.

He finished 39th in his final 2008 start in the fall race at Phoenix International Raceway after getting swept up into a multi-car crash.

Petty is active in many charitable causes, such as Victory Junction, a facility for serious illness and chronic medical condition children, which he established to honor his late son, as well as an annual charity motorcycle ride across the country called the Kyle Petty Charity Ride Across America.

His lone single from this period was "The Other Guy", which led to appearances on Hee Haw and opening for acts such as Randy Travis and The Oak Ridge Boys.

A music video for the song was produced, featuring Petty playing an acoustic guitar in front of his father's No.