Background: To evaluate the demographic characteristics, sexual risk behaviours, and ocular manifestations of ocular syphilis, focusing on differences between human immunodeficiency virus (HIV)-positive and HIV-negative individuals. Methods: This retrospective study included patients diagnosed with ocular syphilis at the Uveitis Clinic, Cipto Mangunkusumo Kirana Eye Hospital, from October 2023 to November 2024. Demographic, behavioural, and clinical manifestations were reviewed. Comparative analyses were performed at initial presentation to our referral centre between HIV-positive and HIV-negative patients with ocular syphilis. Results: Forty-seven patients (81 eyes) were analysed, 78.7% (n = 37) being HIV-positive. Most were male (93.6%) with a median age of 35.3 years. Promiscuous sex without commercial sex workers was significantly associated with HIV positivity (p = 0.029) and was frequent among men who have sex with men (MSM) with HIV-coinfected individuals. Over half (54.1%) of HIV-positive individuals were newly diagnosed during their uveitis workup. Vitritis was common (86.4% of eyes), while anterior chamber inflammation (29.2% vs. 6.3%, p = 0.048) and posterior uveitis with necrotizing retinitis (47.7% vs. 25%, p = 0.085) were more frequent in HIV-positive than HIV-negative patients. Conclusion: Ocular syphilis showed marked male predominance (9:1) and high HIV co-infection rates. HIV positivity was linked to high-risk sexual behaviours, particularly among MSM with non-commercial partners. Clinical manifestations were diverse, with certain findings, with several findings—especially anterior chamber and necrotizing posterior inflammation—more frequent in HIV-co-infected individuals. © 2026 Taylor & Francis Group, LLC.