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Squamous cell carcinomas (SCC) account for the majority of all primary oropharyngeal carcinomas. These tumors can progress locally as well as metastasize to lymph nodes, the lung, bone, and liver. Metastases of primary laryngeal SCC to the small bowel is exceedingly rare and portends a poor prognosis as they often present with catastrophic symptoms. HPV-related head and neck SCC (HNSCC) is a peculiar subset of all HNSCC, and available data from prospective studies suggest better survival outcomes with HPV-related HNSCC compared to non-HPV-related HNSCC. In this article, we report the case of a patient who was managed at a tertiary hospital for a HPV-related laryngeal SCC with metastases to the small bowel presenting as small bowel obstruction (SBO). We also conducted a systematic review of HNSCC metastatic to small bowel with a focus on relation to HPV. We identified 13 reported cases of HNSCC metastatic to the small bowel. Of these, only 1 case was positive for p16 (a marker of HPV infection in HNSCC). We present the second case of HPV-related HNSCC with metastases to the small bowel.