The clinical, radiological, and operative factors of recurrent chronic subdural hematoma (CSDH) were retrospectively analyzed in 116 patients with CSDH in 134 hemispheres, treated by one burr hole surgery. The correlation of recurrence was evaluated with personal and clinical factors such as age, sex, history of head injury, and interval from onset of initial symptoms to hospitalization; laboratory findings such as bleeding tendency and liver function; computed tomography (CT) findings such as hematoma density and brain atrophy; and operative findings such as additional procedures and postoperative residual air. The recurrence group (RG) included 10 hemispheres (7.5%) in 10 patients (8.6%). The interval from onset of symptoms to hospitalization was significantly shorter in the RG than in the nonrecurrence group (NRG). Headache was more frequently seen in the RG than in the NRG. Density of hematoma on CT was classified into five types: Low, iso, and high density, niveau, and mixed, and the incidence of recurrence was 0%, 2.3%, 17.2%, 12.5%, and 6.5%, respectively. Larger amounts of residual air in the postoperative hematoma cavity were associated with recurrence of CSDH. CSDH that progresses rapidly in the acute stage and appears as high density on preoperative CT is associated with a high incidence of recurrence. Intraoperative air invasion to the hematoma cavity should be avoided to prevent recurrence.