Surgical pyloroplasty or pyloromyotomy are often performed during esophagectomy with a view of improving gastric conduit drainage. However, the clinical importance of this is not clear, and some centers opt to omit this step. The aim of this meta-analysis is to compare the rates of pulmonary complications, anastomotic leak, mortality, delayed gastric emptying, and the need for further pyloric intervention, in patients undergoing esophagectomy with and without a drainage procedure. A database search of Medline, EMBASE, and Cochrane Library was performed to identify randomized control trials and cohort studies published between 2000 and 2020 which compared outcomes of esophagectomy with and without drainage procedures. A random-effects meta-analysis model was used to compare the rates of pulmonary complications, anastomotic leak, mortality, delayed gastric emptying, and the need for further pyloric intervention. Three randomized and 12 non-randomized publications were identified, comprising a total of 2339 patients. No significant differences were found between the two groups with regard to pulmonary complications (RR 1.02 [95% CI, 0.78-1.33], p = 0.91), anastomotic leak (RR 1.14 [95% CI, 0.80-1.62], p = 0.48), mortality (RR 0.53 [95% CI, 0.23-1.26], p = 0.15), delayed gastric emptying (RR 0.98 [95% CI, 0.59-1.62], p = 0.93), and the need for further pyloric intervention (RR 1.99 [95% CI, 0.56-7.08], p = 0.29). Where post-operative pyloric treatment is available on demand, surgical pyloric drainage procedures may not have any significant clinical impact on patient outcomes for patients undergoing esophagectomy, though further good-quality randomized controlled trials are needed to confirm this.