* Professor Moriarty: Considered Holmes' arch-nemesis, Moriarty is a criminal mastermind who frequently outsmarted Holmes, even leading to his apparent death in "The Final Problem."
* Irene Adler: Known as "The Woman" in "A Scandal in Bohemia," Adler was a brilliant and cunning woman who managed to outwit Holmes by using her intelligence and charm to outmaneuver him.
* The "Napoleon of Crime": A cunning and enigmatic criminal who used complex and elaborate plans to deceive Holmes. This character appeared in "The Adventure of the Empty House" and other stories.
* The "Greek Interpreter": This cunning criminal managed to frame a man for murder and escape justice, even though Holmes was investigating the case.
* The "Dancing Men": While not explicitly a villain, the creator of the "Dancing Men" cipher outsmarted Holmes initially by cleverly encoding a message that seemed impossible to decipher.
It's worth noting that while these individuals outsmarted Holmes at times, he often managed to uncover their plans and bring them to justice eventually. This reinforces the idea that while Holmes is incredibly intelligent, he is also vulnerable to the cunning and unexpected actions of his opponents.