Objective To report the clinicopathologic features of 19 new cases of oral syphilis in a population from Brazil. Study Design Oral syphilis cases diagnosed in the last 4 years were retrieved and a descriptive analysis was performed. Results There were 11 men and eight women, with age ranging from 16 to 60 years (mean of 27.2 years). The most common clinical appearance of oral syphilis was of white plaques or ulcers usually affecting the tongue, buccal mucosa, palate, and lower lip. Two patients showed cervical lymphadenopathy, with skin involvement of the hands and abdominal region. Fourteen patients were subjected to biopsy and microscopically, all cases revealed perivascular and subepithelial lymphoplasmacytic infiltrate in a vascularized connective tissue, which was covered by stratified squamous epithelium with acanthosis, hyperkeratosis, and microabscesses. The diagnosis of oral syphilis in all patients was confirmed by serologic positivity for Venereal Disease Research Laboratory (VDRL) and fluorescent treponemal antibody absorption (FTA-ABS). Eighteen patients showed oral manifestations of secondary syphilis and 1 patient of primary syphilis. Conclusions Patients with oral syphilis from Brazil showed similar clinicopathologic features compared with other countries. Oral manifestations may be the first sign of syphilis.