(1) Background: The jejunum is primarily used for distal pancreatic stump anastomoses after central pancreatectomy (CP). The study aimed to compare duct-to-mucosa (WJ) and distal pancreatic invagination into jejunum anastomoses (PJ) after CP. (2) Methods: All patients with CP and jejunal anastomoses (between 1 January 2002 and 31 December 2022) were retrospectively assessed and compared. (3) Results: 29 CP were analyzed: WJ—12 patients (41.4%) and PJ—17 patients (58.6%). The operative time was significantly higher in the WJ vs. PJ group of patients (195 min vs. 140 min,p= 0.012). Statistically higher rates of patients within the high-risk fistula group were observed in the PJ vs. WJ group (52.9% vs. 0%,p= 0.003). However, no differences were observed between the groups regarding the overall, severe, and specific postpancreatectomy morbidity rates (pvalues ≥ 0.170). (4) Conclusions: The WJ and PJ anastomoses after CP were comparable in terms of morbidity rates. However, a PJ anastomosis appeared to fit better for patients with high-risk fistula scores. Thus, a personalized, patient-adapted technique for the distal pancreatic stump anastomosis with the jejunum after CP should be considered. At the same time, future research should explore gastric anastomoses’ emerging role.