Background: Chronic calcific pancreatitis (CCP) is a debilitating condition that often leads to intractable abdominal pain and pancreatic dysfunction. The Frey procedure is a surgical technique aimed at managing pain and improving pancreatic function in patients with CCP. This study evaluates the outcomes of head coring in CCP patients without a head mass. Methods: A combined prospective and retrospective analysis was performed on 75 patients with CCP who underwent the Frey procedure. Patients were evaluated for pain relief, glycemic control, exocrine function, and weight gain during a six-month follow-up period. Results: Pain relief was achieved in 90.7% of patients, with a significant reduction in Visual Analog Scale (VAS) scores from a mean of 8.2 ± 0.7 preoperatively to 1.1 ± 0.5 postoperatively. Of the 8 diabetic patients, 37.5% showed improvement in glycemic control, with reduced insulin requirements and lower HbA1c levels. Among the 6 patients with preoperative steatorrhea, 60% experienced symptom improvement. Weight gain of more than 5 kg was observed in 69.3% of patients. Complications occurred in 13.3% of patients, including pulmonary issues, wound infections, and one case of jejunojejunal intussusception. Histopathological examination revealed chronic pancreatitis in 74 patients, with one case showing pancreatic malignancy. Conclusions: The Frey procedure is an effective surgical intervention for providing pain relief, improving endocrine and exocrine function, and promoting weight gain in CCP patients without a head mass. The procedure demonstrates low morbidity and offers favorable short-term outcomes. However, careful consideration of potential pancreatic malignancy is necessary, and long-term follow-up is essential to monitor for complications and assess the durability of results.