Background Patients presenting with concurrent headache types present a challenge in diagnosis and subsequent treatment. Cervicogenic headache, concussion, and cervical artery dysfunction may present with similar and often overlapping symptoms and impairments. These include but are not limited to neck pain and headache, dysphagia, dysarthria, diplopia, dizziness, drop attacks, nystagmus, nausea, and nervousness. Case Presentation A 40-year-old female presented with a history of insidious onset left-sided neck pain, occipital headache, and subsequent concussion history. Additional symptoms included intermittent dizziness, nausea/vomiting, and intolerance of noise/computers. Cervicogenic symptoms were ruled in with upper cervical mobility tests. Vestibular symptoms were provoked with Vestibular/Ocular Motor Screening. Risk factors were carefully considered; while the patient demonstrated no increase in symptoms with vertebral artery insufficiency testing, potential vascular involvement could not be completely ruled out. Discussion This case details the clinical reasoning applied to the differential diagnosis and treatment of a complex headache presentation in the presence of conflicting symptoms. JOSPT Cases 2022;2(2):103–108. doi:10.2519/josptcases.2022.10676