The 1999 TranSouth Financial 400 was the fifth stock car race of the 1999 NASCAR Winston Cup Series season and the 43rd iteration of the event.

This situation makes it very challenging for the crews to set up their cars' handling in a way that is effective at both ends.

[3] Jeff Gordon, driving for Hendrick Motorsports, would set the fastest time in the session, with a lap of 28.688 and an average speed of 171.416 mph (275.867 km/h).

[5] The final practice session, sometimes referred to as Happy Hour, was held on Saturday, March 20, after the preliminary 1999 Diamond Hill Plywood 200 NASCAR Busch Series race.

[3] Mark Martin, driving for Roush Racing, would set the fastest time in the session, with a lap of 29.821 and an average speed of 164.904 mph (265.387 km/h).

[7] Jeff Gordon, driving for Hendrick Motorsports, would win the pole, setting a time of 28.398 and an average speed of 173.167 miles per hour (278.685 km/h) in the first round.