Ranging from localised to generalised, infectious to neoplastic, autoimmune, or miscellaneous aetiology; lymphadenopathies have a wide array of clinical presentations. Assessment of the true pathobiology of lymphadenopathies is a challenging process specially cases with lymphadenopathy due to malignancies in the head and neck region. A multitude of masking signs and symptoms make it even more complicated. However, a correct diagnostic workflow facilitates easy evaluation of such lymphadenopathies. Although, the correct clinical examination may help to achieve correct diagnosis in some lymphadenopathy cases, some suspicious and unexplained lymphadenopathies warrant further investigations. This chapter clearly focuses on the clinical, diagnostic, and histopathologic spectrum of head and neck lymphadenopathies arising in oral cancer and stressing upon the pathways of lymphatic spread of malignancy along with a multitude of lymph node characteristics which play a key role in diagnosis.