The aims of this study were to evaluate the efficacy of two different phlebotonic therapies, preoperatively administered in advanced hemorrhoidal disease (HD) patients with recommendation for surgery, and to assess patient satisfaction after treatment. In this prospective observational study, 100 patients were preoperatively treated either with micronized purified flavonoid fraction (group A) or sublingual nano-emulsion flavonoid (group B). HD symptoms, local inflammation signs and patients’ satisfaction were evaluated at baseline visit (T0), after 4 weeks of therapy (T1) and 8 weeks after its discontinuation (T2). In group A, a significant improvement for all HD symptoms and inflammation signs was observed after therapy (T1), followed by a reduction of efficacy in T2, except for itching and edema. In group B, therapy had a significant benefit on symptoms and local inflammation at T1, which persisted after its discontinuation for all symptoms, and edematous hemorrhoids. In both groups, the satisfaction rate was “good” in 60% of patients and patients were statistically significant more satisfied at T1 compared with T2 (p = 0.0001). No adverse events were recorded. Preoperative treatment was safe and useful to optimize patients’ clinical condition prior to surgery.