Megamind is completely based around this trope. The entire plot of the movie begins with our supervillain is fighting his superhero like always, but then he actually manages to win, and the hero dies. Nobody comes to save the town, the villain takes over, and everyone is sad, however the villain comes to wonder what to do next. The rest of the film is basically what might follow with the villainsuddenly not having an arch rival.
At the end of Cars, villain Chick Hicks wins the final race of the season. Subverted because Chick would never have won fairly; he had to run one of the racers off the road, totaling him, and McQueen deliberately lost the race to help said guy. Chick is booed off the stage for being a dirty cheater, and doesn't get the sponsorship contract that normally goes along with victory.
Pinocchio averts this trope with Stromboli, Lampwick and Monstro, but plays it straight with "Honest" John Worthington Foulfellow, his sidekick Gideon, and the Coachmen, who all win (though in the Coachmen's case this is because nobody opposes him). In the Video Game however you actually fight the Coachman where he gets a Disney Villain Death.