The 1989 TranSouth 500 was the fifth stock car race of the 1989 NASCAR Winston Cup Series and the 33rd iteration of the event. The race was held on Sunday, April 2, 1989, before an audience of 45,000 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. At race's end, Jackson Bros. Motorsports driver Harry Gant would manage to dominate the late stages of the race to take his 10th career NASCAR Winston Cup Series victory, his only victory of the season, and his first victory in 90 NASCAR Winston Cup Series races.^[1][2][3][4] To fill out the top three, Robert Yates Racing driver Davey Allison and Hendrick Motorsports driver Geoff Bodine 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, March 30, at 2:00 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, March 31, at 10:30 AM 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,^[5] 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.

Mark Martin, driving for Roush Racing, would win the pole, setting a time of 30.523 and an average speed of 161.111 miles per hour (259.283 km/h) in the first round.^[6][7]

No drivers would fail to qualify.