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The purpose of this article is to report a case of upper eyelid mechanical ptosis caused by silicone oil migration in a Jordanian patient after pars plana vitrectomy and intraocular silicone oil injection. A 20-year-old male patient was referred to the oculoplastic clinic for the management of a left upper eyelid swelling and complete ptosis that developed 12 years after pars plana vitrectomy and silicone oil placement for retinal detachment secondary to perforating eye injury. Eye examination showed upper eyelid swelling and a complete ptosis induced by the weight of inflammatory tissue and silicone oil, as proved by histopathologic examination. We presumed that silicone oil had leaked through the pars plana vitrectomy ports or through a subtle traumatic perforation of the posterior segment, which might have been aggravated by increased intra-ocular pressure postoperatively. In conclusion, mechanical ptosis caused by silicone oil migration after retinal detachment surgery is rare and this is one of the few reports in the literature.