Trigeminal trophic syndrome (TTS) is a cause of facial ulceration that occurs secondary to trigeminal nerve injury. This condition mimics other causes of facial ulceration, often leading to misdiagnosis. This case series presents the clinical features, diagnostic approaches, and treatment outcomes of five patients with TTS to help improve understanding of this rare condition and diagnostic accuracy. Review of these cases demonstrates the most common area of ulceration was the nose, a female predominance, and an age of presentation of middle-aged to older adults. Four patients had biopsy results revealing an absence of malignant or infectious cause of facial ulceration. Ulceration typically develops years after nerve injury and may persist for months to years. Treatment typically involved topical antibiotics, neurology consultation, and four of the five patients underwent surgical repair for the treatment of TTS. Early recognition and an individualized multidisciplinary therapeutic approach are vital in improving patient outcomes and quality of life, as well as preventing recurrence in patients with TTS.