Simultaneous bilateral total knee arthroplasty (TKA) might be associated with higher postoperative morbidity and mortality rates compared with staged bilateral TKA. However, risk factors for surgical complications and reoperations following simultaneous bilateral TKA remain elusive. We conducted this retrospective, single-surgeon case series from 2010 through 2019. A total of 1561 patients who underwent simultaneous bilateral TKA procedures were included. The outcome domains included 30-day and 90-day readmission events for medical or surgical complications and 1-year reoperation events. We performed logistic regression analysis and backward stepwise selection to identify possible risk factors, including age, sex, body mass index, diabetes mellitus (DM), rheumatoid arthritis, American Society of Anesthesiologist (ASA) classification, Charlson Comorbidity Index (CCI), receiving venous thromboembolism (VTE) prophylaxis, or blood transfusion. The overall 30-day, 90-day readmission, and 1-year reoperation rates were 2.11%, 2.88%, and 1.41%, respectively. Higher CCI score (CCI = 4+) was a risk factor for 90-day readmission (aOR: 2.783; 95% CI 0.621–12.465), 90 day readmission for surgical complications (aOR: 10.779; 95% CI 1.444–80.458), and 1 year reoperation (aOR: 4.890; 95% CI 0.846–28.260). Other risk factors included older age, higher ASA level, DM, and receiving VTE prophylaxis. In conclusion, high CCI scores were associated with increased risks of surgical complications and reoperations following simultaneous bilateral TKA procedures.