Peritonsillar abscesses (PTAs), colloquially termed quinsy, are a frequent complication of tonsillitis, typically presenting unilaterally with distinctive clinical features. However, bilateral PTAs, though rare, pose diagnostic complexities due to their atypical manifestations. This study discusses a 15-year-old patient’s case with bilateral PTA and conducts a thorough review of 28 documented cases of bilateral PTAs, outlining clinical features, management options, and outcomes. Most bilateral PTA occurrences were observed in male patients across a broad age spectrum. Notably, some cases showed a positive association with acute Epstein-Barr virus (EBV) infection. Various drainage techniques, including incision and drainage, needle aspiration, and tonsillectomy, were employed, each demonstrating effectiveness in different scenarios. Systemic antibiotics targeting group A β-hemolytic streptococci and anaerobes were frequently administered as adjunctive therapy. The study underscores the importance of early consideration and swift surgical intervention, especially in septic individuals lacking uvula dislocation. Routine EBV serology is recommended during diagnosis to inform treatment decisions accurately. While successful outcomes were observed in all reviewed cases, caution is advised regarding potential complications of deep neck abscesses, necessitating vigilant management.