Meningiomas are the commonest benign intracranial tumors and frequently present with a gradual onset of neurological deficits; however, their acute presentation with hemorrhagic onset appears to be a rare event. Nonetheless, because the mainstay of treatment is early surgical evacuation, prompt diagnosis of this rare category of intracranial hemorrhage is imperative. The purpose of this single-center study was to investigate the radiological characteristics and proposed a new bleeding classification for guiding diagnosis and treatment. A total of 19 consecutive patients diagnosed with hemorrhagic meningioma were enrolled in this retrospective study. Intracranial extra-axial mass, tumor-associated hemorrhage, and peritumoral brain edema were the three main radiological features. The site of tumor-associated hemorrhage included peritumoral space, subarachnoid space, subdural space, brain parenchyma, and/or intratumor. Based on the anatomical relationship between meningioma and hematoma, the spontaneous hemorrhage stemming from meningiomas were further summarized into three bleeding patterns involving purely intratumoral hemorrhage (type I), purely extratumoral hemorrhage (type II), and combined intra/extratumoral hemorrhage (type III); moreover, the type III hemorrhage usually came from the type I bleeding that extended into the surrounding regions. The symptoms in type I patients were generally mild, and early surgery was performed following adequate preoperative evaluations; the symptoms in type II patients were sometimes mild and may be sometimes moderate to severe, so early or emergency surgery was chosen according to the patients’ clinical statuses; almost all type III patients had moderate to severe symptoms, and these patients usually needed emergency surgery. In addition, the patients with different bleeding types may have different pathological mechanisms underlying the bleeding. Apart from being convenient for diagnosis, this concise and practical bleeding classification could offer some implications for the treatment strategy and facilitate understanding of the associated mechanisms.