Silicone oil migration into the periorbital tissues occurs rarely after vitreo-retinal surgery and two cases are reported. The first case was a 48-year-old woman who presented with a blind painful right eye, upper eyelid swelling, and ptosis after multiple vitreo-retinal surgeries. Diffuse infiltration of silicone oil in the upper eyelid and anterior orbit was found during evisceration, mainly around the plate of a Baerveldt glaucoma valve. In the second case, a 69-year-old man with prior right scleral rupture underwent silicone oil tamponade for retinal detachment and presented with right upper eyelid swelling due to multiple silicone oil granulomas within the orbit. Open globe injury and glaucoma drainage devices both appear to facilitate extraocular migration of silicone oil that results in marked orbital infiltration and inflammatory response.