Background: Currently, there are different competing techniques for the treatment of Zenker’s diverticulum (ZD). To improve patient selection, we compared endoscopic laser-assisted diverticulotomy (ELAD) with transcervical myotomy (TCM) with regard to possible risk factors for treatment failure. Methods: Data of ZD patients (n = 104) treated between 2004 and 2016 with either TCM (38%) or ELAD (62%) were analyzed retrospectively. Univariate and multivariate analyses were performed. Results: TCM is associated with a higher morbidity (27.8% vs. 10.2%; p = 0.095) but lower recurrence rate (7.3% vs. 19.3%; p = 0.095). Preoperative reflux disease (OR 8.755; p = 0.021) was identified as an independent risk factor for complications. Conclusions: Although short-term outcome and symptom relief are similar, TCM tends to have a higher complication rate but better long-term results. Preoperative reflux disease is an independent risk factor for postoperative complications.