Syphilis has been classically divided into three clinical stages. The chancre that appears at the site of inoculation is referred to as the primary stage. The secondary stage is characterized by systemic involvement and the appearance of a disseminated maculopapular rash. Cardiovascular, neurologic and gummatous lesions characterize tertiary syphilis. The simultaneous presentation of primary and secondary syphilis has been reported because the chancre can persist into the secondary stage, especially in HIV positive patients. Although syphilitic alopecia is a rare manifestation of secondary syphilis it is an important differential diagnosis in the evaluation of patients with patchy hair loss. This article aims to present the case of a 34-year-old HIV-positive male patient that presented simultaneous primary and secondary syphilis associated with syphilitic alopecia and acute bacterial folliculitis.