Background/Objectives: The anesthetic block of the sensory branches of the superficial cervical plexus (SCP) renders a specific area of the face, head, and anterior neck insensible and painless. Chronic pain in these areas can be difficult to diagnose and treat. In this report, we briefly review the existing evidence on the topic of the SCP block (SCPB) to set the context for our research. We then share our own clinical experience with the SCPB for managing chronic pain syndromes from both cancerous and non-cancerous etiologies. Methods: We first performed a comprehensive literature search and narrative review of clinical cases and studies that utilized the SCPB as an analgesic technique. We then conducted a retrospective case series of all patients who received a SCPB at our pain clinic since 2020. Results: Our literature review found only a few cases reported, with most of them focusing on acute painful emergencies and perioperative pain syndromes and only very few addressing chronic pain. In our pain clinic, 14 patients received one or more SCPBs for chronic pain management. In 42% of these cases, the pain was related to cancer. The most common areas of pain corresponded to the regions supplied by the transverse cervical and greater auricular nerves. The procedures were uneventful in all cases, and patients rated them as effective and worthwhile 71% of the time. Conclusions: Despite the lack of high-quality studies on SCPBs in pain management, the authors’ experience suggests that it is a valid minimally invasive alternative for managing chronic face, head and neck pain.