Objective and Importance: The clinical and radiographic presentations of epidermoid cyst (EC) and arachnoid cyst (AC) are distinct for most cases. We present 2 cases with spontaneously intracystic hemorrhage illustrating the occasional difficulty one can encounter in distinguishing EC and AC. Clinical Presentation: Patient 1 is a woman who presented with left facial numbness, headache, and ataxia. Computerized tomography presented with an isodensity, whereas magnetic resonance image (MRI) presented with short T1 and long T2 signals with a fluid-fluid level. Patient 2 is a woman who presented with vertigo, numbness in the left face and tongue. Computerized tomography presented with hyperdensity, whereas MRI presented with homogeneous short T1 and short T2 signals. Intervention: Patient 1 was initially diagnosed with EC with spontaneous intracystic hemorrhage. Operative and pathologic findings revealed AC. Patient 2 was initially diagnosed with AC. However, 4 months later, the lesion presented itself with an enlarged cyst with nodules inside, indicating the diagnosis of EC. Conclusions: To differentiate between EC and AC with spontaneously intracystic hemorrhage is sometimes difficult. However, some features facilitate the differentiation. Fluid-fluid levels on MRI, especially on T2-weighted images, indicate the diagnosis of AC, whereas nodular signals in the background of hematoma indicate the diagnosis of EC. Operative findings of cheese-like content and white, thick capsules with or without granulation tissue adhesive to the peripheral tissue indicate EC, whereas transparent arachnoid-like capsules without solid content indicate AC. Microscopic examination will confirm the diagnoses.