Background/Objectives: Efforts have been made toward primary or secondary stroke or transient ischemic attack (TIA) prevention. However, little attention has been paid to recurrent stroke or TIA. This study investigated risk factors for multiple or single recurrent stroke or TIA. Methods: Data from 3646 patients with ischemic stroke or TIA were obtained from the Korea University Ansan Hospital Stroke Center between March 2014 and December 2021, using the prospective institutional database of the Korea University Stroke Registry. The associations between clinical features and recurrent stroke or TIA were assessed using bivariable and multivariable Cox models. Results: Recurrent stroke or TIA was associated with male sex (adjusted hazard ratio (HR) 1.95, 95% confidence interval (CI) 1.42–2.80), hypertension (HR 1.49, 95% CI 1.00–2.23), diabetes mellitus (HR 1.54, 95% CI 1.13–2.13), an etiologic subtype of transient ischemic attack (HR 1.88, 95% CI 1.09–3.16), white matter changes (HR 1.62, 95% CI 1.05–2.38), and cerebral microbleeds (HR 1.79, 95% CI 1.26–2.59). Multiple recurrent stroke or TIA was associated with male sex (HR 3.86, 95% CI 1.94–11.55), diabetes mellitus (HR 2.40, 95% CI 1.31–4.53), and anemia (HR 4,58, 95% CI 2.31–10.44). Conclusions: Given the risk factor profiles for recurrent stroke or TIA, risks differed among patient subgroups and were based on multiple or single recurrences. It may exert an effect as a prognostic indicator in the high risk of recurrences.