The 1989 Holly Farms 400 was the 26th stock car race of the 1989 NASCAR Winston Cup Series season and the 40th iteration of the event. The race was originally scheduled to be held on Sunday, October 1, 1989, but due to rain throughout the race's weekend, the race was postponed until Sunday, October 15.^[1][2] The race was held in North Wilkesboro, North Carolina at the North Wilkesboro Speedway, a 0.625 miles (1.006 km) oval short track. The race took the scheduled 400 laps to complete. On the final lap of the race, a battle between Richard Childress Racing driver Dale Earnhardt and King Racing driver Ricky Rudd that had been culminating since the final restart of the race on lap 398 came to a head. Heading into the first turn, Rudd would dive-bomb Earnhardt, which led Rudd into Earnhardt's car, spinning both cars. As a result of the spin, the third place driver at the time, Hendrick Motorsports driver Geoff Bodine, would manage to avoid the wreck and take the victory. The victory was Bodine's seventh career NASCAR Winston Cup Series victory and his only victory of the season.^[3][4][5][6] Rudd and Earnhardt would finish ninth and tenth, respectively.

In the driver's championship points battle, leader Rusty Wallace was able to increase his lead over Earnhardt by two points to make his lead over Earnhardt 37 points with three races left in the season. Had Earnhardt either won or taken second in the race, Earnhardt would have retaken the driver's championship lead from Wallace.^[7]

North Wilkesboro Speedway is a short oval racetrack located on U.S. Route 421, about five miles east of the town of North Wilkesboro, North Carolina, or 80 miles north of Charlotte. It measures 0.625 mi (1.006 km) and features a unique uphill backstretch and downhill frontstretch. It has previously held races in NASCAR's top three series, including 93 Winston Cup Series races. The track, a NASCAR original, operated from 1949, NASCAR's inception, until the track's original closure in 1996. The speedway briefly reopened in 2010 and hosted several stock car series races before closing again in the spring of 2011. It was re-opened in August 2022 for grassroots racing.

Qualifying was originally scheduled to be split into two rounds.^[8] The first round was scheduled to be run on Friday, September 29, at 3:00 PM EST. 31 cars would manage to set times in the session before the session was stopped due to rain.^[9][10] Originally, qualifying would have been condensed into one round and ran the next day on Saturday, September 30. However, due to persistent rain, qualifying was cancelled and the lineup was set by the current 1989 owner's points. As a result, Richard Childress Racing driver Dale Earnhardt would win the pole.^[11][12]

Four drivers would fail to qualify.