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Introduction: The retropharyngeal carotid artery (RCA) is a rare anatomical variant where the carotid artery resides in the retropharyngeal space. The co-occurrence of RCA and significant atherosclerotic stenosis of the carotid bifurcation is even rarer. Recognizing this anatomy is crucial because of the increased risk of adverse events during procedures such as intubation or oropharyngeal surgery. Furthermore, differentiating between the fixed and dynamic forms is essential for guiding appropriate diagnostic and therapeutic strategies. A scoping review was undertaken, and two cases of RCA and significant internal carotid artery stenosis requiring a surgical approach were presented. Materials and Methods: EMBASE and OVID were systematically searched for studies reporting data on RCA and significant internal carotid artery stenosis. The Preferred Reporting Items for Systematic Reviews and Meta-Analyses Extension for Scoping Reviews (PRISMA-ScR) was followed, and we presented two case reports of RCA and significant internal carotid artery stenosis requiring surgical treatment, treated at the Division of Vascular Surgery, IRCCS MultiMedica, Sesto San Giovanni, Milan, Italy. Results and Discussion: Among the 22 papers identified by the scoping review, 6 case reports were ultimately included in the analysis, supplemented by our two cases. The review and the added cases highlight significant heterogeneity in the clinical presentation and management of RCA with stenosis. Therapeutic options include carotid endarterectomy (CEA), transfemoral carotid artery stenting (TF-CAS), and transcarotid artery revascularization (TCAR). Also, the diagnostic with dynamic 3D-CT angiography during swallowing would be important in some symptomatic cases to document mechanical compression by the hyoid bone or thyroid cartilage (dynamic RCA), which standard static imaging failed to detect. Conclusions: Due to the rarity of the condition, no high-level evidence (RCTs) exists. Treatment decisions are based on the qualitative assessment of anatomical risk and isolated case reports. Standard interventions (CEA and TF-CAS) are generally considered high-risk. The final management choice must be individualized based on technical feasibility, neurological risk, and the determination of whether the pathology is fixed or dynamically compressive.