Gumma is a characteristic lesion of tertiary syphilis that is rare nowadays, but still rarer is squamous cell carcinoma (SCC) arising from it. A 74-year-old male presented with throat pain and nasal twang with a past history of genital ulcer. Examination revealed a well-defined ulcer with a perforation of 1.5 cm over the hard palate with induration and nodularity at the margins. This patient also had leukoplakia over the ventral aspect of the tongue. His treponema pallidum hemagglutination assay was positive, and biopsy revealed well-differentiated SCC from the lesion over the palate and leukoplakia with dysplasia from the lesion over the tongue. Patient is on treatment from radiotherapy. To conclude, this is a unique presentation of syphilitic gumma with palatal perforation with SCC and syphilitic leukoplakia with Ca in situ over tongue. Thus, serology for syphilis should be done in all patients with SCC of the oral cavity.