Background Different techniques have been described for esophagogastric anastomosis. Over the past decades, surgeons have been improving anastomotic techniques with a gradual shift from hand-sewn to stapled anastomosis. Nowadays, circularstapled (CS) and linear-stapled (LS) anastomosis are commonly used during esophagectomy. Methods PubMed, MEDLINE, Scopus, and Web of Science were searched up to June 2022. The included studies evaluated short-term outcomes for LS vs. CS anastomosis in patients undergoing esophagectomy for cancer. Primary outcomes were anastomotic leak (AL) and stricture (AS). Risk ratio (RR) and standardized mean difference (SMD) were used as pooled effect size measures whereas 95% confidence intervals (95%CI) were used to assess relative inference. Results Eighteen studies (2861 patients) were included. Overall, 1371 (47.9%) underwent CS while 1490 (52.1%) LS. Compared to CS, LS was associated with a significantly reduced RR for AL (RR = 0.70; 95% CI 0.54-0.91; p < 0.01) and AS (RR = 0.32; 95% CI 0.20-0.51; p < 0.0001). Stratified subgroup analysis according to the level of anastomosis (cervical and thoracic) still shows a tendency toward reduced risk for LS. No differences were found for pneumonia (RR 0.78; p = 0.12), reflux esophagitis (RR 0.74; p = 0.36), operative time (SMD −0.25; p = 0.16), hospital length of stay (SMD 0.13; p = 0.51), and 30-day mortality (RR 1.26; p = 0.42). Conclusions LS anastomosis seems associated with a tendency toward a reduced risk for AL and AS. Although surgeon's own training and experience might direct the choice of esophagogastric anastomosis, our meta-analysis encourages the use of LS anastomosis.