Robotic platforms are increasingly utilized in surgery, offering unique technical advantages, though there is a scarcity of difficulty scoring systems (DSS) for these procedures. DSS aids in understanding operative complexities and enhancing preoperative planning. With IRB approval, data were collected on 200 consecutive adult patients who underwent robotic pancreaticoduodenectomy at a high-volume institution from 2019 to 2022. Linear regression was employed on clinical variables to analyze operative time and estimated blood loss as markers of surgical complexity. Weighted scoring system was developed using significant linear coefficient values, and an ANOVA analysis created the difficulty-level grouping system. Significant variables affecting operative time and/or EBL included: history of alcoholism, preoperative endoscopic intervention, tumor size, nodal disease on preoperative imaging, pancreatic duct dilation. These factors created the DSS ranging from 0 to 33. Group 1 (0-8, n = 9), Group 2 (9-20, n = 145), Group 3 (21-26, n = 37), and Group 4 (27-33, n = 9) showed significant differences in age, history of alcoholism, preoperative jaundice, tumor size, nodal disease, and operative metrics. Our novel DSS for robotic pancreaticoduodenectomy effectively predicts intraoperative challenges and aids in preoperative planning. Future steps include validating the system internally and externally.