Background: Anticoagulants are commonly prescribed in medical practices and could be of significant harm in the case of medication errors. We conducted a retrospective observational study to determine the frequency and consequences of the therapeutic duplication of anticoagulants (TDA). As a secondary objective, we aimed to determine the characteristics of the population in which TDA occurs. Methods: We conducted a retrospective observational study among admitted patients who concomitantly received at least two anticoagulants from August 2017 to August 2018. Results: A total of 107 patients with TDA are included in the research. The patients with TDA have a mean age of 73. The TDA population has a high rate of associated comorbidities with 69% of patients having arterial hypertonia, 40% with chronic kidney disease, 26% with a history of malignancy, and 20.5% with a history of stroke. More than 65% of patients were under anticoagulation before admission, mostly due to atrial fibrillation. The TDA occurred in more than 95% of cases in the first week or the last week of hospitalization. Patients had a high risk of bleeding prior to the TDA-event with about 62.5% of TDA patients having a HAS-BLED score at least 3. A total of 8 patients showed a significant Hemoglobin (Hb)-drop of at least 10 g/L within 24 h after TDA-event. Two patients had a new or worsened hematuria following TDA-event. Conclusion: TDA occurred in 0.8% of patients who were under anticoagulation and in 6.7% of patients who received direct oral anticoagulants (DOACs). TDA led in about 7.4% of cases to hemoglobin-relevant bleeding. The old patients with significant comorbidities and a high HAS-BLED score were mainly affected. The female gender and presence of anemia independently predicted the occurrence of bleeding following TDA.