The 42nd International 500-Mile Sweepstakes was held at the Indianapolis Motor Speedway on Friday, May 30, 1958. The event was part of the 1958 USAC National Championship Trail, and was also race 4 of 11 in the 1958 World Championship of Drivers.

The race is best known for a massive first-lap, 15-car pileup that resulted in the death of fan-favorite driver Pat O'Connor.

Jimmy Bryan was the race winner. This marked the first time that one car would carry two drivers to separate wins at the race, in back-to-back years, with Sam Hanks winning the previous year's race in the same car.

The race featured young rookie A. J. Foyt's debut at Indy. On lap 148, he spun in an oil slick, blew out the tires, and dropped out of the race.

Juan Manuel Fangio, the 46-year-old five-time Formula One Drivers' World Champion, had set pole and fastest lap in the first F1 race of the season, then was kidnapped in Cuba, and skipped the Monaco and Dutch Grands Prix he had already won in earlier years. He arrived at Indy under much fanfare as he attempted to qualify for the Indy 500 and score points towards the '58 World Championship. He practiced early in the month, but withdrew when he realised that neither the Kurtis Kraft #54 (with Novi engine) nor the #77 Offy-powered car gave him a chance to win. These cars were qualified by others for the last row only, proving Fangio's point. He soon retired from Formula One as his Maserati team was off pace compared to Ferrari and new British challengers.

Time trials were scheduled for four days.

For the second year in a row, the starting grid was assembled single-file in the pit lane. The cars were instructed to pull away and assemble into the official eleven rows of three after they entered the racing surface. Confusion occurred on the pace lap, however, as the three drivers of the front row (Dick Rathmann, Ed Elisian, and Jimmy Reece) pulled away, and inadvertently escaped the pace car. The three cars were alone, and rather than wait for the grid to catch up, they rushed around to catch up to the back of the field. Sam Hanks pulled the pace car off the track and into the pits, but chief starter Bill Vanderwater displayed the yellow flag to wave off the start. An extra pace lap was allowed, and the front row re-took their position at the front of the pack. By the time Hanks was ready to pull the pace car back out on the track, the field had re-formed, and Vanderwater gave them the green flag.

At the start, Dick Rathmann took the lead in turn 1, Ed Elisian was second, and Jimmy Reece third. As the cars battled into turn three, Elisian spun and took Rathmann to the outside wall, triggering a huge 15-car pileup. Reece braked and was hit from behind by Pat O'Connor. O'Connor's car sailed fifty feet in the air, landed upside down and burst into flames. Several other cars spun to the wall and into the infield. Jerry Unser touched wheels with Paul Goldsmith, and flipped over the outside wall. Unser suffered a dislocated shoulder.