Background: s/Aims: The benefits of nasogastric intubation after pancreaticoduodenectomy are not well understood, and it remains unclear which patients may need nasogastric intubation in the immediate postoperative period. This study evaluated the effectiveness of nasogastric intubation following pancreaticoduodenectomy and identified factors influencing the reintubation rate. Methods: We conducted a retrospective case-control cohort study involving adult patients who underwent pancreaticoduodenectomy for either benign or malignant periampullary disease, with a 90-day follow-up. Patients were divided into two groups: the nasogastric tube (NGT) was removed at the end of the procedure (NGT-removed group, n = 110; case group) or retained during the postoperative recovery (NGT-retained group, n = 100; control group). Results: The overall postoperative complication rate (grades I–IVb) was 40.4%. The only significant difference between the groups was a higher incidence of nausea and vomiting in the NGT-removed group (p = 0.02). Additionally, 14.8% of patients required NGT reinsertion postoperatively. No preoperative or intraoperative factors were found to influence the NGT reinsertion rate. Although patients requiring reinsertion experienced a higher rate of postoperative complications, no factor remained significant in the multivariate analysis. Conclusions There were no significant differences in clinical outcomes, reinsertion rates, or postoperative complications between the two groups, indicating that the removal of the NGT after pancreaticoduodenectomy is safe. However, univariate analysis revealed that postoperative complications significantly affected the need for NGT reinsertion, suggesting that nasogastric decompression may be crucial for patients at high risk for complications.