The 1986 Miller High Life 400 was the second stock car race of the 1986 NASCAR Winston Cup Series and the 32nd iteration of the event. The race was held on Sunday, February 23, 1986, before an audience of 30,000 in Richmond, Virginia, at Richmond Fairgrounds Raceway, a 0.542 miles (0.872 km) D-shaped oval. The race took the scheduled 400 laps to complete.^[1]

In what is considered to be one of the most controversial finishes in NASCAR history, Junior Johnson & Associates' Darrell Waltrip and Richard Childress Racing's Dale Earnhardt engaged in a battle for the victory. With four laps left, Waltrip made a pass on Earnhardt in the second turn, passing him on the left. However, Waltrip did not fully clear Earnhardt by the third turn. In the third turn, Earnhardt spun out Waltrip, sending the two into a crash that included numerous other cars behind them. As a result, the next driver behind the two who managed to avoid the wreck, Wood Brothers Racing's Kyle Petty, was declared the winner in improbable fashion. The victory was Petty's first career NASCAR Winston Cup Series victory and his only victory of the season. To fill out the top three, King Racing's Joe Ruttman and the aforementioned Earnhardt finished second and third, respectively.^[2][3]

Richmond International Raceway (RIR) is a 3/4-mile (1.2 km), D-shaped, asphalt race track located just outside Richmond, Virginia in Henrico County. It hosts the Monster Energy NASCAR Cup Series and Xfinity Series. Known as "America's premier short track", it formerly hosted a NASCAR Camping World Truck Series race, an IndyCar Series race, and two USAC sprint car races.

Qualifying was scheduled to be split into two rounds, with the first round scheduled to be held on Friday, February 21, at 3:00 PM EST, and the second round scheduled to be held on Saturday, February 22, at 11:30 AM EST. The first round would have set positions 1-20, while the second round would have set positions 21-30 for drivers who had not locked in during the first round.^[4] However, the first round was immediately cancelled due to mist.^[5] The second round was then attempted to be run, but was then also cancelled after 23 cars made runs due to rain.^[6]

As a result of qualifying being cancelled, the starting lineup was set by a rained-out procedure. Positions 1-18 were given based on the current 1986 owner's points, positions 19-20 were given to winners in the 1985 NASCAR Winston Cup Series who had not qualified by owner's points, and positions 21-30 were given to the teams who had both had their entry blanks received by NASCAR and had checked in at the NASCAR on-track check-in hauler the earliest. In addition, one provisional was given out of the maximum two allowable.^[6] As a result of this system, Hendrick Motorsports' Geoff Bodine won the pole.^[7] Four drivers failed to qualify.