The team debuted at the 1985 Daytona 500, entering the No. 55 and No. 66 cars with Copenhagen and Skoal Smokeless Tobacco sponsorship and driven by brothers Benny and Phil Parsons respectively. Both cars suffered engine failures in that race, but the Parsons brothers became fixtures with the team through the late 1980s. Phil Parsons scored the team's first victory in 1988 at the Winston 500, winning despite running out of fuel during the race.
In 1989, the team expanded to two cars by signing Harry Gant away from Mach 1 Racing, with Gant's Skoal sponsorship following him to the No. 33. Gant won at Darlington that season and finished seventh in points, while Phil Parsons posted a modest campaign before departing for Morgan-McClure Motorsports.
When Richard Jackson split from the partnership in 1990 to form his own operation and took the No. 55 equipment, the team was renamed Leo Jackson Motorsports and continued with Harry Gant in the No. 33. Gant had modest success in 1990, winning at Pocono, but the 1991 season became the defining chapter of the team's history.
Gant, at age 51, won four consecutive races late in the 1991 season — at Michigan, Darlington, Dover, and Martinsville — spawning the memorable "Life Begins at 51" campaign as Gant became the oldest winner in NASCAR history. He finished third in the points standings that year. Gant followed that performance with two more victories in 1992 and a fourth-place points finish, establishing the Leo Jackson team as a legitimate contender during those seasons.
Gant's final seasons with the team in 1993 and 1994 yielded poles but no wins, and he announced his retirement at the end of 1994. During that farewell year, the team groomed replacement Robert Pressley, who ran three races in a No. 54 car. Pressley moved to the No. 33 full-time in 1995, finishing runner-up to Ricky Craven for Rookie of the Year honors.
By 1996, Leo Jackson was contemplating retirement and sought a buyer for the team. His crew chief at the time, Andy Petree, purchased the organization. After briefly fielding Todd Bodine to finish the 1996 season, Petree selected Ken Schrader as his driver beginning in 1997. Schrader delivered consistent top-ten results and two pole positions at New Hampshire, finishing tenth in points in both 1997 and 1998.
For 1999, Petree expanded to a two-car operation, adding Kenny Wallace in the No. 55 with Square D sponsorship. Wallace posted a career-best second-place finish at New Hampshire but managed only a 22nd-place points finish overall. The team also lost its long-standing Skoal sponsorship from the No. 33, replaced by Oakwood Homes. Schrader departed to pursue other opportunities, and Joe Nemechek was hired for the 2000 season.
The team reached its operational peak in 2001 when Bobby Hamilton, Schrader's replacement, won at Talladega in the No. 33, and Nemechek won at Rockingham Speedway — giving the organization two victories in a single season. However, Oakwood Homes experienced financial difficulties and withdrew sponsorship, destabilizing both cars.
The 2002 season proved difficult as the team raced intermittently without a full-time sponsor. Hamilton departed following a broken shoulder sustained in a crash, and the team failed to attract replacement sponsorship. Christian Fittipaldi started the 2003 Daytona 500 in the No. 33, finishing 35th, and Paul Menard made one additional start at Watkins Glen. In 2004, Petree and Menard attempted the NASCAR Busch Series to attract Cup sponsorship, but Menard signed with Dale Earnhardt Inc. and took his family's funding with him. Petree subsequently auctioned off all team equipment, with most assets — including the No. 33 — purchased by Kevin Harvick Incorporated for Busch Series use.
Leo Jackson Motorsports and its successor, Andy Petree Racing, produced some of the most memorable late-season drives of the early 1990s through Harry Gant's remarkable four-race winning streak in 1991. The operation sustained competitiveness across nearly two decades despite modest resources and multiple ownership transitions, and served as a launching pad for several Cup Series careers through the Skoal sponsorship program.