Background: Radiologic imaging has become integral in not only the detection and diagnosis of subdural hematoma, but also in guiding potential treatment options. Particularly, in the arena of chronic subdural hematoma, which has conventionally been managed via surgical drainage, although is shifting toward procedural intervention with embolization of the middle meningeal artery. This paper aims to review the imaging manifestations of subdural hematoma as a function of chronicity, standardized methods of measurement, and identifying the middle meningeal artery and its clinically significant variant anatomy as it pertains to embolization planning. Methods: A literature search using key terms and titles was conducted for articles containing imaging characteristics of subdural hematoma, approaches to measurement, and middle meningeal artery anatomy as the primary focus. Results: The expected evolution of subdural hematoma over time encompasses a broad array of imaging characteristics. Attempts at standardizing hematoma measurements include width, volume, and midline shift. Given the implication of the middle meningeal artery in potential therapeutic embolization, familiarity with its anatomy is vital not only for mapping access, but also for delineating possible dangerous collaterals. Conclusions: Equipped with a more comprehensive approach to characterizing subdural hematoma, the radiologist will be able to curate findings of greater utility to the clinician.