Tandem spinal stenosis (TSS) is an entity which refers to spinal canal diameter narrowing in at least two distinct regions of the spine. When symptomatic, management of TSS is controversial. In this study, we present a consecutive series of patients with symptomatic TSS and report diagnostic and surgical challenges. We retrospectively reviewed a consecutive series of N = 8 patients with symptomatic TSS who underwent surgical treatment in at least one region of the spine. Patients presented with multiple complaints, including neurogenic claudication, progressive gait disturbances, and signs of radiculopathy and/or myelopathy, among others. Modified Japanese Orthopedic Association (mJOA) and Oswestry Low Back Pain Disability Questionnaire (ODI) were obtained in pre- and postoperative period. Electroneurophysiological examinations were limited to patients whose clinical and radiological signs were not sufficient to determine which region was more affected. From 2015 to 2018, we included N = 8 consecutive patients with TSS who underwent surgery by a staged approach. The stenosis was localized in the cervical and lumbar region in six patients (75%) and in the cervical, dorsal, and lumbar level (triple TSS) in two patients (25%). Four patients (50%) underwent cervical and lumbar surgery, two (25%) underwent cervical surgery alone, and two (25%) were operated in all three involved regions. Surgical treatment allowed an improvement of the mean mJOA score (from 12.5/17 to 15/17) and mean ODI score (from 41 to 28%). TSS represents a clinical, diagnostic, and surgical challenge. We recommend to systematically obtain electrophysiological and radiological examinations and then to perform a staged surgery, beginning at the most symptomatic region.