Clear cell acanthoma (CCA) and squamous cell carcinoma (SCC) represent distinct entities within dermatological oncology, each posing unique diagnostic and therapeutic challenges. CCA is a rare, benign epidermal growth, often not associated with human papillomavirus (HPV) infection, whereas SCC, a more aggressive form of skin cancer, has been linked to both ultraviolet (UV) exposure and HPV. Understanding the co-occurrence of these conditions in a single patient can enhance diagnostic accuracy and therapeutic outcomes. We report a 64-year-old male who underwent an operation for a verruciform lesion in the right groin, which was diagnosed as HPV-positive CCA alongside keratinised SCC. A literature search across January 2024 revealed limited evidence directly linking HPV to CCA, suggesting a need for further investigation. The speculative association between HPV and CCA warrants deeper exploration, especially considering the potential for HPV to contribute to lesion development through indirect mechanisms. The coexistence of CCA and SCC in an elderly patient presents a unique clinical scenario. This emphasises the need for vigilant diagnosis and tailored treatment strategies, highlighting the gap in understanding the pathogenesis of CCA, particularly its potential association with HPV. Further research is crucial for elucidating the complex interactions governing these conditions and for developing targeted interventions.