Meningiomas are relatively common primary adult brain tumors. They are slow-growing, highly vascular, and graded according to histology, phenotypic and genotypic features. We present a case of a 66-year-old male with a history of tongue squamous cell carcinoma, which presented multiple risk factors for cardiovascular and thromboembolic events. A brain lesion was initially detected on a computed tomography (CT) scan and later characterized by magnetic resonance imaging (MRI). The multidisciplinary team decided to maintain surveillance due to the lack of associated symptoms. Upon expansion in size and acute intralesional hemorrhage seen on follow-up imaging, the patient was submitted to surgical excision. The histopathological testing determined it to be an atypical meningioma. Two months later, the patient received stereotactic radiotherapy, and a post-surgical MRI showed no evidence of tumor recurrence. This case report describes a rare occurrence of intratumoral hemorrhage in a meningioma during surveillance, highlighting the importance of vigilant monitoring and consideration of potential risk factors for hemorrhagic events.