Objective: Endovascular embolization using non-adhesive agents (e.g., ethylene vinyl alcohol copolymer with suspended micronized tantalum dissolved in dimethyl sulfoxide; Squid, Balt Extrusion) is an established treatment of brain arteriovenous malformations, dural arteriovenous fistulas, and hypervascular neoplasms. Middle meningeal artery (MMA) embolization is a relatively new concept for treating chronic subdural hematomas (CSDH). This study aimed to evaluate the safety and effectiveness of the use of Squid in the endovascular treatment of CSDH. Methods: Embolization was offered to patients with CSDH with minimal or moderate neurological deficits and patients who had previously undergone open surgery to evacuate their CSDH without a significant effect. Distal catheterization of the MMA was followed by embolization of the hematoma capsule with Squid 12 or Squid 18. Safety endpoints were ischemic or hemorrhagic stroke and any other adverse event of the endovascular procedure. Efficacy endpoints were the feasibility of the intended procedure and a ≥ 50% reduction of the maximum depth of the CSDH confirmed by follow-up computed tomography (CT) after >3 months. Results: Between November 2019 and July 2021, 10 patients (3 female and 7 male, age range 42–89 years) were enrolled. Five patients had bilateral hematomas, and five patients had previously been operated on with no significant effect and recurrent hematoma formation. The attempted embolization was technically possible in all patients. No technical or clinical complication was encountered. During a post-procedural follow-up (median 90 days), 10 patients improved clinically. A complete resolution of the CSDH was observed in 10 patients. The clinical condition of all enrolled patients during the so-far last contact was rated mRS 0 or 1. Conclusion: A distal catheterization of the MMA for the endovascular embolization of CSDH with Squid allowed for the devascularization of the MMA and the dependent vessels of the hematoma capsule. This procedure resulted in a partial or complete resolution of the CSDH. Procedural complications were not encountered.