Superman Should Have Won His Famous Race With the Flash
Superman's famous race with the Flash should have ended with the clear winner: Superman. The self-proclaimed "Fastest Man Alive" has raced against the Last Son of Krypton many times in the comics and on film (most notably in 2017's Justice League), but in his first race, no one exactly knew who would win. But readers of Superman #199 knew that the only reason why Superman didn't win...was because he was too busy being Superman.
Writers of both Superman and the Flash have steadily increased the super-speed of each hero over the years. Superman, who started as "faster than a speeding bullet!" can now fly around the world in seconds. Flash could run faster than the speed of sound - now, he can outrun time itself. But the question of DC's fastest hero was very much up in the air until Superman #199 by Jim Shooter and Curt Swan, where the two were called upon by the UN secretary for a race to raise money for undeveloped countries across the world. Both heroes quickly agreed, and the race was on - but not without some criminal trouble.
Both Superman and the Flash circumnavigated the Earth three times on a path over many obstacles and terrain (including snowy mountains, dense jungles, and across the ocean), and in the interest of fairness, Superman was forbidden to fly. Unbeknownst to both, rival crime syndicates from American and Europe have placed billion-dollar bets on each participant, and manipulate the race to fix the outcome. They've also hired multiple scientists who engineer various traps for each hero - but they all inevitably fail. During a particularly close clash in Canada, the Flash trips, hits his head on the ice, and is knocked out cold.
Superman stops dead in his tracks and - without a single second of hesitation - changes into Clark Kent and helps the Flash to his feet. Clark claims he was covering the race in a helicopter, and even though no helicopter can be seen (on that panel or any other), the Flash thanks him and speeds ahead. He easily could have pulled ahead, but Superman's too altruistic to leave a friend behind - even if it could potentially cost him the race. When the two realize bets have been placed on them to win, they agree to tie - racing across the finish line at the same moment, denying the rival syndicates any chance of their money.
Flash and Superman would race many times throughout DC comics continuity, usually for charity or another common goal. In the current DC timeline, Flash is most definitely the faster hero, going fast enough to travel through time in Flashpoint and even travel faster than instant teleportation. But during the height of the Silver Age, Superman would have soundly defeated the Flash if not for the fact that he stopped to help his opponent - as befits anyone with the name Superman.