Objective: This study investigated the radiological, clinical, and surgical factors linked to the risk of endoscopic recurrence following ileocolic resection for Crohn’s disease. Materials and Methods: We conducted a retrospective analysis of data from all patients who underwent primary ileocecal resection for Crohn’s disease in a single colorectal unit between 2004 and 2020. We analyzed the potential risk factors subdivided by the clinical, radiological, and surgical factors associated with morphological recurrence, as detected by endoscopy within 2 years after surgery. Cox regression was employed to ascertain the risk factors associated with such recurrence. Results: In total, 63 patients were included, and 24 (38%) had endoscopic recurrence. The age of the patient at the time of surgery was identified as a significant clinical factor associated with the risk of recurrence (HR: 1.04; p = 0.003), indicating that the probability of recurrence increases by 1% as the surgical age increases each year. The radiological factors associated with an increased risk of recurrence included localization in the distal ileum (HR: 3.526; p = 0.015), the number of pathological small-bowel segments affected by the disease (HR: 1.15; p = 0.004), and the total length of the pathological intestinal segment (HR: 1.002; p = 0.014). The presence of granulomas (HR: 6.003; p = 0.004) and the length of the resected bowel (HR: 1.01; p = 0.003) were surgical factors associated with a higher risk of recurrence. Conclusions: This study delineated several clinical, radiological, and surgical factors that serve as predictors for the endoscopic recurrence of Crohn’s disease after surgery.