Ocular syphilis presenting initially as various manifestations of intraocular inflammation is a rare but an important manifestation of syphilis. Ocular phenotypes are varied and mimic other infectious and non-infectious ocular diseases. Uncertainties exist in optimal management of ocular manifestations of syphilis due to a lack of evidence from randomized controlled trials. In this article we report seven cases of syphilis representing a spectrum of ophthalmic manifestations and highlight key issues around diagnosis and management. We underscore the importance of interdisciplinary approach by ophthalmologists and genitourinary (GU) physicians in improving the outcome of this subgroup of patients in the absence of robust evidence.