In the realm of fault-tolerant quantum computing, stabilizer operations play a pivotal role, characterized by their remarkable efficiency in classical simulation. This efficiency sets them apart from non-stabilizer operations within the computational resource theory. In this work, we investigate the limitations of classically-simulable measurements, specifically POVMs with positive discrete Wigner functions which include all stabilizer measurements, in distinguishing quantum states. We demonstrate that any pure magic state and its orthogonal complement of odd prime dimension cannot be unambiguously distinguished by POVMs with positive discrete Wigner functions, regardless of how many copies of the states are supplied. We also give the asymptotic error probability for distinguishing the Strange state and its orthogonal complement. Moreover, we prove that every set of orthogonal pure stabilizer states can be unambiguously distinguished via POVMs with positive discrete Wigner functions, which is different from the existence of an unextendible product basis in entanglement theory. Our results reveal intrinsic similarities and distinctions between the quantum resource theory of magic states and entanglement in quantum state discrimination. The results emphasize the inherent limitations of classicallysimulable measurements and contribute to a deeper understanding of the quantum-classical boundary.