Warning: Contains SPOILERS for The Batman.
The Riddler does the one thing that the Joker didn't in The Dark Knight, his victory is more spiritual. However, Robert Pattinson's less experienced Bruce Wayne is put through the wringer by Paul Dano's Riddler, and the ultimate outcome proves that he's the first on-screen villain to truly beat Batman.
The Dark Knight concludes with Batman foiling the Joker's plan to have ordinary Gotham citizens prove the immorality of humanity. However, Heath Ledger's Clown Prince of Crime then brags about his ace in the hole: Harvey Dent. By corrupting Harvey and turning him into Two-Face, the Joker claims that he has defeated Batman in their moral conflict by proving that even the best person in Gotham can be broken and manipulated into doing terrible things. By contrast, Batman is too late to stop Riddler's plot in The Batman, and Gotham City is flooded. Though the Caped Crusader prevents Riddlers' allies from assassinating the mayor, Gotham is in ruins by the film's end: as a result, Riddler wins.
Batman movies have never shown a supervillain winning in such an unambiguous way before Riddler in The Batman. Riddler outsmarts Batman, and Bruce is too late to stop him from flooding the city, no doubt killing many innocent civilians in the process. It is difficult to say that Batman won simply because he was able to prevent the mayor's death when Riddler so seamlessly destroyed the rest of the city. Though Gotham will likely rebuild, Riddler's victory is the greatest defeat ever dealt to a live-action Batman.
Prior to The Batman, the Joker's moral victory in The Dark Knight is the closest evil plan that can be considered a loss for Batman. However, the reveal that Harvey Dent transformed into a murderer, though brutal to Bruce and Jim Gordon due to their partnership with him, is a more personal victory based on Batman and the Joker's conflicting ideologies. By contrast, the Joker's plan to test the people of Gotham still fails, and his corruption of Dent is more like a consolation prize than a fully-fledged victory.
Riddler, on the other hand, achieves his goal of killing and exposing all the corrupt Gotham officials (his version of the moral mission) and launches a successful major terrorist attack on the entire city. It is, therefore, apparent that Riddler is a more successful villain than the Joker. Though both villains test Bruce on both a moral and physical level, only one of them is able to pull off both parts of their plan.
Paul Dano has made comic book movie history by portraying the first villain to truly defeat Batman. The Batman presents a younger Bruce Wayne, who simply isn't experienced enough to completely stop a major threat like Riddler. The older Bruce of The Dark Knight (and the people of Gotham) overcome the Joker, and he only beats Batman on a philosophical level by breaking Harvey Dent, essentially cheating to win. By contrast, the Riddler wholly outsmarts him and envelops Gotham in a deadly flood, causing untold damage and loss of life and brutally beating the Batman.
