Primary syphilis is characterized by the presence of a chancre and secondary syphilis by the presence of syphilis. The presence of chancres within secondary syphilis have been reported, however, this form of presentation is rare. Patients with synchronous diagnosis of primary and secondary syphilis were included. They underwent a reverse sequence algorithm for syphilis diagnosis with a rapid syphilis test, if positive, a rapid plasma reagin (RPR) or venereal disease research laboratory (VDRL) tests were performed. A total of 15 patients were included. All were men. In primary syphilis, penile chancre predominated in 13 patients (86.6%), and one (6.7%) was in the tongue. In secondary syphilis syphilitic roseola was the most common type of presentation in 10 patients (66.6%), followed by the palmoplantar plaques in 6 patients (40%) and condyloma lata in 2 patients (13.3%). One patient presented alopecia in a “moth-eaten” pattern and this presentation coexisted with a condyloma lata and the palmoplantar plaques. Other patient presented with syphilitic roseola, palmoplantar plaques and condyloma lata. Clinical presentation as coexistent primary-secondary syphilis will become more frequent. First contact physicians and dermatologists would have to take more in consideration infrequent and atypical clinical forms of this disease.