The Man of Steel and The Flash first raced each other in 1967, in Superman #199, by Jim Shooter Curt Swan, and George Klein. Like many of their future races, the pair go up against each other for charity. They competed twice for good causes and, in both instances, the races ended in a tie. The third race featured the pair working together to stop the destruction of planets, with Flash barely crawling in for the win.
Most of their subsequent races have seen similar results, with either Barry Allen or Wally West proving fast enough to outrace Superman. When he really cuts loose, the Flash has even been shown to be able to run circles around Superman.
The friendly rivalry between the pair has transcended comics and appeared in other mediums. The DC Animated Universe version of the Flash was first introduced in a race with Superman in the episode “Speed Demons”. The two also decided to test their powers against one another during one of the post-credits sequences of Justice League. Earlier in the film, Superman had been shown keeping up with Flash, but the movie concluded on a playful note as the pair decided to go all out.
The newest race between Superman and the Flash consists of ten laps around the world, and once more it’s for charity. With the entire world watching, both men give it their all. Although Flash takes an early lead, Superman keeps going and closes the gap. The race takes on an added complication however when Lex Luthor, who is watching the race, analyzes what’s happening and realizes that at his current trajectory, Superman cannot win. So, in another attempt to sway public perception about Superman, Luthor tells the charity that if Superman wins the race, he’ll donate a billion dollars to the foundation. He figures that when Superman loses to the Flash, people will blame him for the charity losing the potential windfall he’s offering.
Thanks to his super-hearing, though, Superman overhears Luthor’s scheme. Deciding that he can’t allow the charity to miss out on all that money, Superman tries his hardest to catch up with the Flash. He doesn’t want to cheat by telling the Flash what’s going on, so Superman pushes his speed to the limits. Thinking about all the impossible things he’s done in the past for a good cause, Superman barrels through the race in its final moments. Superman is able to just barely pull ahead, and crosses the finish line just before Flash. A win that forces Lex to build a massive new home for children.