I've noted elsewhere that technically the first supervillain crossover in comic books is that of the Joker and Catwoman in BATMAN #2 (1940). Yet it's less than satisfying in that Catwoman isn't yet in full supervillain mode, but is just a shady lady with a fancy name, like the Dragon Lady in TERRY AND THE PIRATES.
The first "full-blown" supervillain crossover seems to occur in STAR SPANGLED COMICS #7 (1942), wherein the heroic team of the Star-Spangled Kid and Stripesy contends with two villains who had appeared in previous stories, the Hyde-like Doctor Weerd and the pencil-thin Needle. Though the above page shows the two fiends planning to betray one another when it's expedient, they end up escaping together when foiled by the two heroes. There's also a third brand-new villain in the story, the Assassin, but I suspect he never appears again and so does not function even as a "proto-crossover."
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