Symptomatic cluster-like headaches have been described with lesions of the trigeminal and parasympathetic systems. Here, we report the case of a 44-year-old woman with continuous auricular pain and a positional cluster-like headache associated with red ear syndrome. Clinical data and morphological investigations raised the hypothesis of a neurovascular compression between the C3 root and vertebral artery. Neurosurgical exploration found a fibrosis surrounding both the C3 root and the vertebral artery. The excellent outcome after microvascular cervical decompression suggests a causal relationship between the cluster-like headache and the vertebral constraint on the C3 root.