The 1987 Winston 500 was the ninth stock car race of the 1987 NASCAR Winston Cup Series season and the 18th iteration of the event. The race was held on Sunday, May 3, 1987, before an audience of 135,000 in Lincoln, Alabama at Alabama International Motor Speedway, a 2.66 miles (4.28 km) permanent triangle-shaped superspeedway. The race was shortened from its scheduled 188 laps to 178 due to impending darkness that was caused by a lengthy red flag for debris cleanup and catch fence repairs for an earlier accident.^[1]

By race's end, Ranier-Lundy Racing's Davey Allison had managed to dominate a majority of the race, leading 101 laps when the race was called to take his first career NASCAR Winston Cup Series victory and his first victory of the season.^[2][3] To fill out the top three, Junior Johnson & Associates' Terry Labonte and Wood Brothers Racing's Kyle Petty finished second and third, respectively.

The race is considered to be one of the most influential races in terms of the advancement of auto racing safety. On the 21st lap of the race, Stavola Brothers Racing's Bobby Allison lost his engine, with pieces of his engine cutting his right rear tire at speeds of around 210 miles per hour (340 km/h). The car turned backwards and went airborne, hitting the wall and tearing down a wide stretch of protective fencing to protect fans from accidents. After the car hit the fence, the car was described to have spun "round-and-round like an insane top" per The Atlanta Constitution writer Bill Robinson,^[4] collecting other cars in the accident and the accident itself injuring four spectators; none of them serious.^[5]

The nature of the crash became a source of controversy for NASCAR. In response, NASCAR implemented the mandatory restrictor plate by the start of the 1988 season, which restricted air intake to the engine, made cars considerably slower, and unintentionally ushered in the era of pack racing.^[6]

Talladega Superspeedway, originally known as Alabama International Motor Superspeedway (AIMS), is a motorsports complex located north of Talladega, Alabama. It is located on the former Anniston Air Force Base in the small city of Lincoln. The track is a tri-oval and was constructed in the 1960s by the International Speedway Corporation, a business controlled by the France family. Talladega is most known for its steep banking and the unique location of the start/finish line that's located just past the exit to pit road. The track currently hosts the NASCAR series such as the NASCAR Cup Series, Xfinity Series and the Camping World Truck Series. Talladega is the longest NASCAR oval, a 2.66-mile-long (4.28 km) tri-oval like the Daytona International Speedway, which also is a 2.5-mile-long (4.0 km) tri-oval.

Qualifying was split into two rounds. The first round was held on Thursday, April 30, at 2:00 PM EST. Each driver had one lap to set a time. During the first round, the top 20 drivers in the round were guaranteed a starting spot in the race. If a driver was not able to guarantee a spot in the first round, they had the option to scrub their time from the first round and try and run a faster lap time in a second round qualifying run, held on Friday, May 1, at 2:00 PM EST. As with the first round, each driver had one lap to set a time. For this specific race, positions 21-40 were decided on time,^[7] and depending on who needed it, a select amount of positions were given to cars who had not otherwise qualified but were high enough in owner's points; up to two were given.

Bill Elliott, driving for Melling Racing, managed to win the pole, setting a time of 44.998 and an average speed of 212.809 miles per hour (342.483 km/h) in the first round.^[8] The lap set a new all-time record for the fastest recorded qualifying lap based on average speed; the record still stands as of April 2023.^[9]

Two drivers failed to qualify. One of the drivers who failed to qualify, Blackie Wangerin, crashed during his second-round qualifying run, crashing his only car in the process.^[10] The other driver, Ronnie Sanders, elected to stand on his time; the time was the slowest out of all drivers who ran a lap in both sessions and he did not have enough owner's points for a provisional.^[11]