Squamous cell carcinoma (SCC) of the retromolar trigone (RMT) is a rare but potentially fatal disease that carries a poor prognosis due to its unique anatomic position. RMT SCCs tend to spread to vital nearby structures, including the tonsillar pillar, masticatory muscles, and underlying mandibular bone, even in their early stages, and aggressive treatment is often warranted. This systematic review appraises and qualitatively analyzes all available literature regarding the survival outcomes and prognosis of RMT SCC. Four databases were searched to identify all eligible articles published since January 1980. Of the 1,248 studies, a total of 15 studies representing 4,838 cases met the inclusion criteria. The evaluated patients had a high rate of advanced tumor stage (T3 or T4: 61.4%), lymph node metastasis (38.8%), and mandibular bone invasion (24%) at the time of diagnosis. Aggressive surgical treatments such as lip-splitting (92%), segmental mandibulectomy (61.1%), radical neck dissection (44.1%), and reconstruction using free flaps (49.5%) was undertaken for 92% of the pooled patient population. The mean rates for local, regional, and systemic recurrence were 23.40%, 8.40%, and 8.50%, respectively. The mean 5-year overall survival rate was 38.90%. Osteonecrosis was noted in 11.6% of the 328 patients who received radiotherapy. In conclusion, RMT SCC is generally associated with high recurrence, low survival, and high postoperative complication rates. Early diagnosis and aggressive treatment are thus warranted. However, significant methodological problems hamper current knowledge. Future studies of this topic that use randomized or cohort designs are thus needed.