Bill Elliott's NASCAR Challenge is a video game developed by Distinctive Software and published by Konami and was released for PCs using MS-DOS in 1990, and the Commodore Amiga and Nintendo Entertainment System in 1991. A version for the Apple Macintosh, announced for 1991, was also released.
A very similar game, Bill Elliott's NASCAR Fast Tracks, was released for the Game Boy in 1991 by Konami. In addition, a handheld version based on the series was released in 1991.
This game is the first video game to ever secure the NASCAR license. It features several real NASCAR tracks in the game, such as Watkins Glen and Talladega. This game is also the first ever to feature a real NASCAR driver in an PC game, Bill Elliott.
Bill Elliott's NASCAR Challenge is a simulation of the NASCAR Winston Cup circuit, and thus operates like a racing game. The gameplay action was always through an in-car perspective.
Players could chose to run single races at each track, or run for the season championship. The race distance was chosen by the player, which ranged from 10 miles to the realistic distance of 500 miles for the superspeedway races. In the MS-DOS version, the championship consisted of a visit to each of the eight tracks. In the NES and Game Boy versions, the season championship consisted of each of the four tracks run twice, for a total of eight races. Championship points were awarded consistent to the real-life Winston Cup of the time.
Both the MS-DOS and Nintendo versions allowed the player to setup the car, with effects to be seen. Both of those versions also allowed the player to choose whether they would race with the effect of damage on their car or not. However, a large enough collision with another racecar on the track always would result in the player going out of the race in an out-of-control crash.
Source: Wikipedia, "Bill Elliott's NASCAR Challenge", available under the CC-BY-SA License.