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Major head and neck resections may result in ocular defects that are functionally and/or aesthetically incapacitating. Restoration of the eyelid and orbit must address lateral canthal laxity, midface ptosis, eyelid retraction and ptosis, globe malposition, and dysfunctional lacrimal drainage. Here we discuss lateral canthal reconstruction, midface-lifting, eyelid spacer grafts, gold weight placement, surgical approaches to the orbit, free flap options for orbital reconstruction, and endoscopic lacrimal surgery. Successful outcomes in eyelid and orbital reconstruction depend upon proper knowledge, planning, and multidisciplinary management.