Cervicogenic headache (CGH) is a secondary headache attributed to nociceptive sources in the cervical spine, particularly involving the upper cervical roots (C1–C3) and their convergence with trigeminal afferents in the trigeminocervical complex. Despite its recognition in the third edition of International Classification of Headache Disorders (ICHD-3), CGH is frequently underdiagnosed due to symptom overlap with primary headache disorders. We present the case of a 58-year-old man with a prior history of migraine without aura, who experienced recurrent episodes of unilateral occipital headache during upper respiratory tract infections. These episodes were associated with nasal congestion, pharyngitis, odynophagia, and palpable cervical and retroauricular lymphadenopathy. Headaches lasted 1 to 3 days and featured dull occipital pain radiating to the ipsilateral frontal region, which worsened with neck movement and upon palpation of the occiput. No diagnostic nerve block was performed. Symptoms resolved spontaneously with the resolution of the infection. The temporal relationship between reactive lymphadenopathy and headache episodes suggests intermittent mechanical irritation or compression of the greater occipital nerve (GON), which may contribute to pain through trigeminocervical convergence. Similar mechanisms have been experimentally demonstrated in GON stimulation studies showing referred frontal pain. This case raises awareness of a rarely considered etiology of CGH: nerve compression from reactive cervical lymph nodes. This case underscores the need to recognize reactive lymphadenopathy as a potential trigger for CGH. A detailed neuroanatomical assessment is essential for accurate diagnosis, and further studies are needed to validate the proposed mechanism of headache generation.