The 1988 Southern 500 was the 21st stock car race of the 1988 NASCAR Winston Cup Series season and the 39th iteration of the event. The race was held on Sunday, September 4, 1988, before an audience of 50,000 in Darlington, South Carolina, at Darlington Raceway, a 1.366 miles (2.198 km) permanent egg-shaped oval racetrack. The race took the scheduled 367 laps to complete. In the final laps of the race, Melling Racing's Bill Elliott would manage to fend off Blue Max Racing's Rusty Wallace to the finish to take his 28th career NASCAR Winston Cup Series victory and his fifth victory of the season.^[1][2] To fill out the top three, the aforementioned Rusty Wallace and Richard Childress Racing's Dale Earnhardt would finish second and third, respectively.

Darlington Raceway is a race track built for NASCAR racing located near Darlington, South Carolina. It is nicknamed "The Lady in Black" and "The Track Too Tough to Tame" by many NASCAR fans and drivers and advertised as "A NASCAR Tradition." It is of a unique, somewhat egg-shaped design, an oval with the ends of very different configurations, a condition which supposedly arose from the proximity of one end of the track to a minnow pond the owner refused to relocate. This situation makes it very challenging for the crews to set up their cars' handling in a way that is effective at both ends.

Qualifying was split into two rounds. The first round was held on Thursday, September 1, at 3:00 PM EST. Each driver would have one lap to set a time. During the first round, the top 20 drivers in the round would be 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, September 2, at 2:00 PM EST. As with the first round, each driver would have one lap to set a time. For this specific race, positions 21-40 would be decided on time^[3] and depending on who needed it, a select amount of positions were given to cars who had not otherwise qualified on time but were high enough in owner's points; up to two provisionals were given.

Bill Elliott, driving for Melling Racing, would win the pole, setting a time of 30.577 and an average speed of 160.827 miles per hour (258.826 km/h) in the first round.^[4]

Two drivers would fail to qualify.