Amputation of facial soft tissue, particularly avulsion due to human bite, is an uncommon injury that has severe cosmetic and functional implications. Microsurgical replantation has the potential for superior aesthetic outcomes and restoration of function. We report a case of a 46-year-old male who sustained avulsion injuries from human bites, which included portions of his eyebrow, nose, and upper lip. Artery and vein microvascular replantation was performed on the upper lip. The amputated eyebrow and nasal segments were replanted in a similar fashion to a skin graft. On post-operation day 1, our patient suffered an ischemic stroke followed by a myocardial infarction requiring systemic tissue plasminogen activator (tPA) treatment. Following administration of tPA, there was continuous bloody discharge from the replant sites and the eyebrow, nose, and upper lip began to appear increasingly dusky. Our patient was determined to be a high-risk candidate for immediate revision surgery and he subsequently underwent a six-stage secondary reconstruction. At his most recent four-month follow-up, our patient is satisfied with his cosmetic and functional outcomes. This was a case of failed microvascular upper lip replantation and eyebrow and nasal replacement complicated by stroke and myocardial infarction. The authors review the common complications in replantation, particularly pertaining to upper lip reanastamosis, and discuss a potential novel complication encountered in this case relevant to both free graft and microvascular replantation.