Lymphoepithelial carcinoma (LEC) is a relatively rare skin malignancy associated with sun-exposed areas in older adults. However, it is more commonly found in the nasopharynx and salivary glands. Cutaneous Scalp LEC with associated sub-occipital nodal disease and isolated ipsilateral level V lymphadenopathy, with no other cervical nodal, mucosal, or postnasal disease, in a young adult is exceptionally rare. No such cases exist in literature. Aim We present a 35-year-old male with right level V metastatic malignancy 8 months following excision of a right scalp LEC. PET revealed 2 avid right occipital nodes and an avid right level V node. There were no other avid nodes in the expected basin or distant metastasis. The patient underwent panendoscopy and biopsy of tonsils, BoT, and PNS, with no malignancy. Right MRND and excision of right occipital nodes was undertaken. 2/2 occipital nodes showed LEC. 1/133 neck nodes had LEC, this was at level V with close (0.6mm) margins (no PNI, ENE, or LVS). PORT was administered to the right neck and scalp. Diagnostic and therapeutic challenges are highlighted, underscoring the atypical and aggressive nodal spread in LEC. Methodology Clinical, operative, and radiological data was extracted from EMR. Literature review on PubMed, Ovid, Scopus, and Google Scholar was conducted to compare management strategies across skin LEC cases. Imaging studies and treatment modalities, including surgical and adjuvant therapies, were analysed. Conclusion This case of scalp LEC with sub-occipital nodes and isolated metastasis to a level V node in a young male highlights the potential for atypical nodal spread in HN cutaneous malignancies. The aggressive nature of LEC is emphasised. Findings underscore the importance of thorough assessment in patients with scalp LEC, even when typical lymphatic drainage patterns are absent. The need for individualised treatment planning in younger patients with atypical nodal metastasis is emphasised.