Background: Postoperative disease recurrence is a challenge in Crohn's Disease management, with reported recurrence rates of 70-90% within one year. Early recurrence decreases quality of life and increases reoperation rates. Aims: To compare the time to anastomotic recurrence following ileocolic resection, after End-to-Side, End-to-End, Side-to-Side or Kono-S anastomotic configurations. Methods: A retrospective review of a metropolitan hospital’s electronic health records was conducted. Adult patients who underwent an ileocolic resection for Crohn's Disease between January 2010 and December 2021 (inclusive) with full public follow-up were identified. Chart review for time to recurrence noted in documentation of clinical, endoscopic and surgical recurrence was collated. Kaplan-Meier Survival curves for disease-free time to endoscopic, clinical and surgical recurrence were created. Univariate and multivariate analyses were conducted to identify risk factors for disease-free survival. Results: 44 patients with full public follow-up were identified (of 128 total Crohn's ileocolic resections). The end-to-side anastomotic configuration was found to have the shortest median time to endoscopic and clinical recurrence (163 weeks, 98 weeks). However, there was no significant difference in the time to endoscopic, clinical and surgical recurrence (p=0.242, p=0.580, p=0.262) between anastomotic configurations. End-to-side configuration, emergency surgery, low patient BMI and postoperative immunomodulator monotherapy were found to be significant risk factors for earlier clinical recurrence. Conclusion: Disease-free survival is shorter in patients who receive an end-to-side anastomosis, corroborating the current understanding we have of the role of bowel mesentery in disease propagation and the effect of luminal diameter on disease recurrence.