Background and Objectives: Patients taking anticoagulants, particularly warfarin and non-vitamin K oral anticoagulants (NOACs), face an elevated risk of postoperative bleeding during minor oral surgeries, highlighting the urgent need to identify reliable predictors for bleeding complications. In this study, we evaluated the effectiveness of predictors of bleeding complications in patients receiving anticoagulants who underwent minor oral surgeries. Materials and Methods: The electronic medical and dental records of 206 patients who underwent oral surgery at the University of Ulsan Hospital between 2015 and 2023 were retrospectively reviewed. Patients were categorized into those taking warfarin and those taking NOACs, and postoperative bleeding was determined. Risk factors were statistically analyzed using the chi-square or Fisher’s exact test and Student’s t-test. Results: Among the 206 patients (86 on warfarin, 120 on NOACs), 84 (36 on warfarin, 48 on NOACs) experienced bleeding complications following their procedures. Time in the therapeutic range (TTR) and international normalized ratio (INR) values were significantly associated with bleeding complications in the warfarin group, while the type of NOAC was associated with bleeding in the NOAC group. Perioperative bleeding was significantly correlated with postoperative bleeding in both groups. Conclusions: Taken together, these findings highlight the correlations between postoperative bleeding and specific factors associated with anticoagulant drugs in patients that underwent oral surgery. Identifying these predictors can improve patient management by enhancing pre- and perioperative assessments, reducing the risk of bleeding, and optimizing surgical outcomes.