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Background: A Best Possible Medication History (BPMH) collected by clinical pharmacists is crucial for effective medication review, but, in Italy, it is often left to the nursing staff. This study aims to compare the quality and accuracy of a clinical pharmacist-documented BPMH with the current standard practice of ward staff-collected BPMH in an Italian preoperative surgical setting. Methods: A 20-week prospective observational non-profit study was conducted in a major university hospital. The study comprised three phases: a feasibility, an observational, and an interventional phase. During the feasibility phase, 10 items for obtaining a correct BPMH were identified. The control group consisted of retrospectively analyzed BPMHs collected by the ward staff during the observational phase, while interventions included BPMHs collected by the clinical pharmacist during the third phase. Omissions between the two groups were compared. Results: 14 (2.0%) omissions were found in the intervention group, compared with 400 (57.4%) found in the controls (p < 0.05); data collection was more complete when collected by pharmacists compared to the current modality (98.0% of completed information for the intervention versus 42.6%; p < 0.05). Conclusions: The involvement of a pharmacist significantly reduced the number of omissions in preoperative surgical-collected BPMHs. This intervention holds the potential to decrease the risk of medication errors associated with inaccurate or incomplete BPMHs prior to surgical hospitalization.