Perirectal hematoma (PH) is one of the most feared complications of stapling procedures. Literature reviews have reported only a few works on PH, most of them describing isolated treatment approaches and severe outcomes. The aim of this study was to analyze a homogenous case series of PH and to define a treatment algorithm for huge postoperative PHs. A retrospective analysis of a prospective database of three high-volume proctology units was performed between 2008 and 2018, and all PH cases were analyzed. In all, 3058 patients underwent stapling procedures for hemorrhoidal disease or obstructed defecation syndrome with internal prolapse. Among these, 14 (0.46%) large PH cases were reported, and 12 of these hematomas were stable and treated conservatively (antibiotics and CT/laboratory test monitoring); most of them were resolved with spontaneous drainage. Two patients with progressive PH (signs of active bleeding and peritonism) were submitted to CT and arteriography to evaluate the source of bleeding, which was subsequently closed by embolization. This approach helped ensure that no patients with PH were referred for major abdominal surgery. Most PH cases are stable and treatable with a conservative approach, evolving with self-drainage. Progressive hematomas are rare and should undergo angiography with embolization to minimize the possibility of major surgery and severe complications.