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Syphilis is a sexually transmitted disease with a wide range of clinical manifestations. Given the recent worldwide resurgence of syphilis, it is imperative to recognise various presentations of this great imitator. Apart from the classic ulcerative lesion of primary syphilis, known as a hard chancre, atypical presentations mimicking other diseases are also reported. A patient with carcinoma of the lip who was scheduled for surgery was diagnosed with an extragenital chancre during routine presurgery screening, leading to a change in the treatment plan for the patient. Other patients were initially treated for conditions such as scrotal eczema, psoriasis, and herpes before the correct diagnosis was made. Rare presentations, such as pustular lesions, paraphimosis, and cord-like thickening of the penis, were also observed in this case series. It is important to recognise these atypical manifestations, as doing so may facilitate early diagnosis and prompt management. Nine cases of syphilis in patients who exhibited atypical manifestations are presented in this case series and were diagnosed based on a high index of suspicion aided by laboratory confirmation.