Subdural hematoma is a type of brain bleed characterized by the accumulation of blood beneath the dura matter. It usually occurs as a sequela of a traumatic event or following the use of antiplatelets and/or anticoagulants. The clinical presentation may include symptoms like headache, confusion, ataxia, and hemiparesis. However, it may even be asymptomatic, especially in the elderly population. The presence of subdural hematoma is a relative contraindication to antiplatelet therapy because of the associated risk of worsening bleeding. Hence, acute coronary syndrome or conditions requiring antiplatelet therapy presents a management dilemma when they coexist with subdural hematoma. This paper reports a case of successful use of dual antiplatelets post percutaneous coronary intervention in a patient with spontaneous chronic subdural hematoma. Our patient had a history of coronary artery disease six months prior to stent placement and was on dual antiplatelet therapy. He developed a headache some months later and his neurologist, on evaluating him, made a diagnosis of subdural hematoma, evident on magnetic resonance imaging of the brain. His antiplatelet therapy was discontinued, and he subsequently had a bilateral middle meningeal artery embolization. Following the procedure, a left heart catheterization was done with appropriate interventions for acute coronary syndrome diagnosed at the time of presentation. He was later discharged on dual antiplatelet therapy, followed up on outpatient at scheduled intervals, and was found stable. This case report suggests that individuals with chronic subdural hematoma who may require antiplatelet therapy can still go on to receive the medication after undergoing a bilateral middle meningeal artery embolization. More observational studies are needed to make this the standard of care.