The 1995 TranSouth Financial 400 was the fifth stock car race of the 1995 NASCAR Winston Cup Series and the 39th iteration of the event. The race was held on Sunday, March 26, 1995, in Darlington, South Carolina, at Darlington Raceway, a 1.366 miles (2.198 km) permanent egg-shaped oval racetrack. The race took the scheduled 293 laps to complete. In a wreck-filled race, Morgan–McClure Motorsports driver Sterling Marlin would manage to make a late-race pass for the lead with 12 to go to take his third career NASCAR Winston Cup Series victory and his second victory of the season.^[1][2] To fill out the top three, Richard Childress Racing driver Dale Earnhardt and Roush Racing driver Ted Musgrave 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 Friday, March 24, at 2:30 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 Saturday, March 25, at 10:00 AM EST. As with the first round, each driver would have one lap to set a time. For this specific race, positions 20-38 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 but were high enough in owner's points; which was usually four. If needed, a past champion who did not qualify on either time or provisionals could use a champion's provisional, adding one more spot to the field.

Jeff Gordon, driving for Hendrick Motorsports, would win the pole, setting a time of 28.786 and an average speed of 170.833 miles per hour (274.929 km/h) in the first round.^[4]

Three drivers would fail to qualify: Kenny Wallace, Brad Teague, and Phil Parsons.