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In contemporary criticism, several factors have been adduced by critics to prove that Arthur Conan Doyle’s Sherlock Holmes is a symbol of the Victorian morality. In particular, many of these critics argue that the Victorian readership creates fantastical ideas about Sherlock Holmes as a means to avoid the Real in a Lacanian sense. Put another way, the Victorian society creates what Lacan conceptualizes as the Fantasy, to avoid the Real as the unconscious truth, converging upon conventional detective novels. However, this paper aims to reveal some exceptional cases that traverse conventional narrative structures of detective fiction and the Fantasy, among Sherlock Holmes canon, centering on Doyle’s short story “The Yellow Face” and some of other major works. Moreover, in order to accomplish this, this paper will incorporate the theoretical work of Tzvetan Todorov and Jacques Lacan: typology of the detective fiction and the concept of the Lacanian Real. According to Lacan, the Real emerges when the Symbolic fails. In this regard, this paper points out that there is significant overlap between Todorov’s conventional narrative structures of detective fiction and the Lacanian concept of the Symbolic order in the nature of their fixed structures: even though the Real is “refractory,” there is a possibility to spot the hidden chasm by traversing the fixed structures of the narratives and the Symbolic order. Furthermore, this paper focuses on the faculty of imagination as a possible mechanism for cultivating human sympathy and pursuing the Real within the Symbolic Order of the Sherlock Holmes canon. Further still, envoking sympathy through the imagination, especially in relation to William Blake’s “minute particulars”, provides means to subvert the Sherlock Holmes canon, bringing about the possibility for both a new reading of them and enhancing the faculty of the human imagination.