Prior literature has demonstrated that ipsilateral hindfoot arthrodesis may increase the risk for reoperation after total ankle arthroplasty (TAA) and that simultaneous hindfoot arthrodesis with TAA could result in short-term clinical and radiologic improvements. The purpose of this study is to compare the reoperation rates after TAA with prior hindfoot arthrodesis vs simultaneous arthrodesis and TAA. Patients who underwent primary TAA were identified in the PearlDiver database. Patients were sorted into 2 study cohorts: hindfoot arthrodesis prior to TAA and simultaneous arthrodesis and TAA. Propensity matched control cohorts were identified for each study group. Multivariate analysis was conducted to account for any confounding variables and covariates when identifying differences in complications between cohorts. 297 patients underwent TAA with prior hindfoot arthrodesis and 174 underwent TAA and hindfoot arthrodesis concurrently. The incidence of reoperation (13.8% vs 5.2%, P < .001) and infection (12.6% vs 5.9%, P = .011) for the simultaneous cohort was higher when compared to the matched control cohort. In contrast, there was no statistically significant difference when comparing the prior arthrodesis cohort to the matched control cohort in reoperation rates (5.1% vs 4.7%, P = .787) or infection rates (4.4% vs 4.8%, P = .734). Those undergoing simultaneous procedures had increased incidences of reoperation, wound complications, infection, and emergency department visits (P < .0167) when compared to the TAA with prior arthrodesis cohort. Patients undergoing TAA and hindfoot arthrodesis concurrently were found to have higher rates of reoperation and infection when compared to the matched control cohort . In contrast, there was no difference in these rates in patients undergoing TAA with prior hindfoot arthrodesis compared with their matched control cohort. Patients undergoing simultaneous procedures had increased rates of reoperations, wound complications, infection, and emergency department visits compared to the TAA with prior arthrodesis cohort. Level III, retrospective comparative database study.