The validation of histological prognostic markers in colorectal cancer not only for survival parameters but also for early postoperative outcomes is of paramount importance. The aim of our study was to search for the tumor histopathological (HP) characteristics that may influence the postoperative morbidity, especially the occurrence of anastomotic leakage. Our results indicated that peritumoral inflammatory cell infiltrate appeared to correlate with both anastomotic fistula and overall postoperative complications. Likewise, high-grade and undifferentiated colorectal tumors seemed to be correlated with a higher incidence of postoperative leakage and complications. No relation could be established between the other HP features and the postoperative untoward outcomes.