- Objective: To assess the rate of orthostatic hypotension and factors associated with it among elderly patients who underwent a comprehensive, ambulatory geriatric assessment. Methods: The study included patients 65 years and older who were assessed in the outpatient comprehensive geriatric assessment unit. Data were collected from the computerized medical record including sociodemographic data, lifestyle, falls, blood pressure, BMI, functional and cognitive status, medications, and comorbidity. Results: The study population consisted of 571 patients who underwent assessment over a nine-year period. The mean age was 83.7 ± 6.1, 35.9% were men, and 183 (32.1%) were diagnosed with orthostatic hypotension. Multiple drugs, in general, and multiple drugs with the potential to cause orthostatic hypotension in particular increased the risk for orthostatic hypotension after adjustment for age, sex, chronic comorbidity, and supine systolic blood pressure ≥150 mmHg [odds ratio (OR) = 1.09, 95% confidence interval (CI): 1.03–1.14 and OR = 1.22, 95% CI: 1.08–1.37, respectively]. In addition, α-blockers and calcium channel blockers increased the risk for orthostatic hypotension after similar adjustments (OR = 1.82, 95% CI: 1.01–3.16 and OR = 1.66, 95% CI: 1.11–2.48, respectively). Similarly, two additional drug types increased the risk for orthostatic hypotension: selective serotonin reuptake inhibitors (OR = 2.09, 95% CI: 1.33–3.19) and tricyclic antidepressants (OR = 4.36, 95% CI: 1.85–10.06). There were no specific associations between age, cognitive and functional state, morbidity (as measured by the Charlson Comorbidity Index), and specific diseases, and orthostatic hypotension. Conclusion: The results of the present study reinforce evidence of an association between drug therapy and orthostatic hypotension.