We report the case of an 81-year-old male with synchronous recurrent cutaneous squamous cell carcinoma (SCC) metastatic to the parotid and diffuse large B-cell lymphoma of the head and neck. These malignancies necessitated integrated multidisciplinary treatment within a short time period. Superficial parotidectomy was followed by chemotherapy for lymphoma. The subsequent radiation treatment plan combined both sequential boost to treat the SCC surgical bed to a higher dose compared with the lymphoma, and dose-painting intensity-modulated radiation therapy (IMRT) to differentially dose the areas at risk. The treatment was tolerated well. The restaging scans demonstrated no evidence of either lymphoma or SCC. This case highlights the importance of combined modality treatment for two concurrent aggressive malignancies in the head and neck region. Radiation treatment planning incorporated both sequential boost and dose-painting IMRT to integrate comprehensive treatment for both malignancies.