Objectives: Although mortality after pancreatoduodenectomy for chronic pancreatitis has declined, the complication rate remains high. Today, there is an increasing need to base clinical decisions on the available scientific evidence to provide the best available treatment for the patients. Therefore, we retrospectively analyzed comprehensive preoperative and postoperative characteristics of patients undergoing pancreatic head resection for chronic pancreatitis and performed an outcome analysis to provide prospective selection or managing criteria that could improve the early surgical results. Methods: Data from 168 patients who underwent pancreatic head resection for chronic pancreatitis between October 1993 and November 2008 in our center were retrospectively analyzed. Risk factors for surgical complications were evaluated by multivariate analysis. Results: Perioperative mortality was 0.6%, and surgical morbidity was 14.3%. Multivariate analysis identified hypertension as significant independent risk factor for surgical complications with an odds ratio (OR) of 3.24. We also found protective factors, namely, preoperative exocrine insufficiency (OR, 0.33) and preoperative diabetes (OR, 0.18). Both protective factors might indicate an advanced chronic pancreatitis. Conclusions: As patients undergoing pancreatic head resection are highly selected, the identified risk factors should only individually be considered in the decision to operate.