Background: Anastomotic leakage is one of the most feared complications of rectal resections. The role of drains in limiting this occurrence or facilitating its early recognition is still poorly defined. We aimed to study whether the presence of prophylactic pelvic drains affects the surgical outcomes of patients undergoing rectal surgery with extraperitoneal anastomosis. Methods: PubMed, EMBASE, and the Cochrane Library were systematically searched for randomized controlled trials comparing drained with undrained anastomoses following rectal surgery. We evaluated possible differences on the relative incidences of anastomotic leakage, pelvic collection or sepsis, bowel obstruction, reoperation rate, and overall mortality. A meta-analysis of relevant studies was performed with RevMan 5.3. Results: A total of 760 patients from 4 randomized controlled studies were considered eligible for data extraction. The use of drains did not show any advantage in terms of anastomotic leak (OR 0.99), pelvic complications (OR 0.87), reintervention (OR 0.84) and mortality. Contrariwise, the incidence of postoperative bowel obstruction was significantly higher in the drained group (OR 1.61). Conclusions: The routine utilization of pelvic drains does not confer any significant advantage in the prevention of postoperative complications after rectal surgery with extraperitoneal anastomosis. Moreover, a higher risk of postoperative bowel obstruction can be of concern.