Background/Objectives: Laryngeal squamous cell carcinoma (LSCC) is one of the most prevalent and challenging malignancies of the head and neck. Clinical staging (cTNM) plays a pivotal role in therapeutic decision-making. However, current imaging modalities often fall short, resulting in discrepancies between cTNM and pathological staging (pTNM). This systematic review aimed to critically evaluate the existing literature on the concordance between clinical and pathological staging of LSCC, quantifying staging inaccuracies and highlighting the prevalence of both under- and overstaging at diagnosis. Methods: A comprehensive search of the English-language literature was conducted across multiple databases, including PubMed, Embase, Scopus, the Cochrane Library, and Web of Science. Eligibility was limited to retrospective case series and observational studies reporting sufficient data to directly correlate individual patients’ cTNM and pTNM classifications. Results: Thirty-one studies comprising 7939 patients met the inclusion criteria. The overall concordance rate between cT and pT was approximately 86.43%. The concordance rates between cT and pT were 82.41%, 82.03%, 78.14%, and 89.64% for cT1, cT2, cT3, and cT4, respectively. Most discordant cases in cT2 and cT3 involved understaging at clinical diagnosis. Conclusions: The limited accuracy of clinical staging in reflecting the true extent of disease remains a critical challenge in the management of LSCC. The inability of current imaging techniques to reliably detect the subtle invasion of key anatomical structures contributes to both under- and overstaging, with significant clinical implications. For patients undergoing non-surgical organ-preservation strategies, these inaccuracies may adversely affect oncologic outcomes.