Earnhardt began his Winston Cup career in 1975, making his first start at the Charlotte Motor Speedway in North Carolina in the longest race on the Cup circuit, the World 600. Earnhardt drove an Ed Negre Dodge Charger(#8) and finished 22nd in the race, one place ahead of his future car owner, Richard Childress.

Through 1976 and 1977 Dale continued Sportsman racing while begging the occasional Winston Cup ride. Dale never won any track championships, he moved around too much. He just raced wherever he felt good about going.

This vehicle theoretically launched Dale's career in the stock car series. This was an un-sponsored car owned by Rod Osterlund, which Dale drove in his 6th NASCAR event (actually his 6th ride and 9th start) at Atlanta (Race 29).  Rumors from DEI itself suggest that Dale only drove this in the Busch series, however, Dale Cline in "Remembering Dale Earnhardt" suggests otherwise. This car was driven only once in the last race of the season at Atlanta. Dale qualified 10th, lost a lap twice, and climbed back up to finish 4th out of 6 lead lap cars, against the likes of Darryl Waltrip and Cale Yarborough.

This car (owner Rod Osterlund) brought Dale his first career Winston Cup win, the Southeastern 500 at the Bristol International Raceway on April 1, 1979, in his 16th career start. In his first full-time NASCAR cup season, Earnhardt earned Rookie of the year honours, beating out the likes of Millikan and Terry Labonte, and finished 7th in points, 1081 points behind champion Richard Petty. He claimed four poles in twenty-seven starts and gathered eleven top 5's and seventeen top 10's. The determined Earnhardt's first win was only his third race working with Jake Elder. The young intimidator led in sixteen races, including the Daytona 500 where he finished 8th.The yellow and blue paint scheme is similar to the 80 Monte Carlo with the difference in the Wrangler sponsorship not showing and the Crane Cams logo is on the angle frame.

This year, David Pearson took over in the #2 car after Dale was injured at Pocono. He drove it for something like 4 or 5 races. He did so well in it (finished second once and won a race also) that Dale was beginning to get worried that he may not have a ride.

1981 Wrangler #2 Pontiac: After the first 16 races with Rod Osterlund, Dale would race for the 4th (?) and last time with owner J.D. Stacy, Dale drove the 1981 Pontiac #2 car sponsored by Wrangler, at Daytona, Nashville, Pocono and at the Talladega 500 (race 20). Dale left the team in August to drive the #3 car for Richard Childress, starting at Michigan. This paint scheme is readily identifiable through the 'sergeants stripes' pattern on the hood and the fact that this is a Pontiac. Dale only drove the Pontiac in Winston Cup in the 1981 season.

This is one of only two Ford's Dale drove in the Winston Cup series. Dale claimed 30 starts, one pole, one win, and 7 tops fives culminating in a 12th place finish (one of his worst years). His previous season had been taxing - owner Rod Osterlund sold his team to J.D. Stacy, then Earnhardt transferred to the Richard Childress team. Dale was advised to sign with Bud Moore for the 82 season, where he would acquire the experience and confidence needed to return to Childress's championship-capable team. This paint scheme has no sponsorship on the angle frame. It also has the Wrangler Pony on the rear deck lid.  Dale only finished out of the top 10 in points in two seasons throughout his career. Darrell Waltrip would gain his second Championship this year.

The 1984 year had two versions of the Wrangler Sponsorship, known as the Yellow Trunk and Blue Trunk paint schemes. This is the first year that Dale exclusively drove with the signature#3 number. This, and the other 1984 scheme proved to be the 2nd most difficult collectibles to obtain. The paint scheme itself is unremarkable with just the Wrangler sponsorship. This year Dale became the first two-time consecutive winner at the Talladega 500, taking the lead on the backstretch of the final lap. Dale would finish this season 4th, 243 points behind champion Terry Labonte.

The oddity for this year was the number 3 on the top is italicized in the opposite direction than usual with the bottom to the front instead of the top. Dale did not like the #3 with the top of the three further back than the bottom. He thought that the top leaning forward made the car look faster and the top leaning back made a car look slower.

The Yellow trunk version was uncommon as was the yellow number 3 on the side with the blue siding running forward from the doors to the front fender. Dale drove this car only once at Daytona in 1984. After that race, it was decided that the car would stand out more if they reversed the colors from blue over yellow to yellow over blue, and the rest is history. After that it became the familiar color scheme Wrangler from 1984 through 1987.

The Blue trunk paint scheme was also uncommon in that only the window frame and front hood were yellow with the remainder of the car being blue with yellow number 3's. Later years had the front quarter panels also predominantly yellow.

This is the car in which Dale captured his 2nd Stock Car series championship, out of an eventual 7. 1986 was an incredibly successful season for Dale in the '86 #3 Monte Carlo fast back. Five race wins and a second cup championship. Dale dominated the competition, beating his closest competitors, Darrell Waltrip and Tim Richmond by 288 points. As with the 1986, the Bow Tie Chevy logo is smaller and black where the 87 has a Red larger Bow tie. GM Goodwrench had increased its sponsorship, as can be seen by the decal on the deck lid and for this year, they also had a small GM Goodwrench logo on the angle frame, a hold over from the 1985 version. This was the fastback version of the Monte Carlo. Dale would win this Championship by 288 points over contender Darrell Waltrip.