PURPOSE: In this study, we evaluated the role of various anastomoses in surgical recurrence for patients with Crohn disease (CD). METHODS: We analyzed data retrospectively from consecutive laparotomy cases involving complicated CD between 1991 and 2008. Clinical data were compared in terms of reoperation-free survival (RFS) according to the types of anastomoses, the materials used for the anastomoses, and the operating surgeon. RESULTS: Of 233 patients with entero-enteric or entero-colic anastomoses, 199 (85%), 11 (5%), and 23 (10%) experienced side-to-side (SS), side-to-end (SE), and end-to-end (EE) anastomoses, respectively. The SS group had the following characteristics: more extensive bowel involvement, frequent obstruction, and greater stapler use; the SS anastomoses were also frequently made by specialized surgeons (P < 0.001–0.004). EE anastomoses were frequently made by general surgeons using a hand-sewing technique (P < 0.001). No differences in RFS were noted among the 3 groups according to the type of anastomosis and the operating surgeon. However, the hand-sewn group showed better RFS than the stapler group (P = 0.04). CONCLUSION: The roles of the anastomotic configuration, the material used, and the operating surgeon were not significantly correlated with reoperations or complications in our retrospective CD cohort, irrespective of the higher risk of anastomosis site stricture for EE anastomoses.