Background: The outcomes of patients with colorectal cancer greatly depend on the quality of their surgical care. However, relying solely on a single quality indicator does not adequately capture the multifaceted nature of modern perioperative care. A new tool—“Textbook Outcome” (TO)—has been suggested to provide a comprehensive evaluation of surgical quality. This study aims to examine how TO affects the long-term outcomes of colorectal cancer patients who are scheduled for surgery. Methods: The data of all patients undergoing elective colorectal cancer resection with primary anastomosis at two major cancer treatment centers in Lithuania—Vilnius University Hospital Santaros Klinikos and National Cancer Institute—between 2014 and 2018 were entered into the prospectively maintained database. The study defined TO as a composite quality indicator that incorporated seven parameters: R0 resection, retrieval of ≥12 lymph nodes, absence of postoperative complications during the intrahospital period, hospital stay duration of fewer than 14 days, no readmission within 90 days after surgery, no reinterventions within 30 days after surgery, and no 30-day mortality. Long-term outcomes between patients who achieved TO and those who did not were compared. Factors associated with failure to achieve TO were identified. Results: Of the 1524 patients included in the study, TO was achieved by 795 (52.2%). Patients with a higher ASA score (III-IV) were identified to have higher odds of failure to achieve TO (OR 1.497, 95% CI 1.203–1.863), while those who underwent minimally invasive surgery had lower odds for similar failure (OR 0.570, 95% CI 0.460–0.706). TO resulted in improved 5-year overall—(80.2% vs. 65.5%, p = 0.001) and disease-free survival (76.6% vs. 62.6%; p = 0.001) rates. Conclusions: Elective colorectal resections result in successful TO for 52.5% of patients. The likelihood of failure to achieve TO is increased in patients with a high ASA score, while minimally invasive surgery is associated with higher TO rates. Patients who fail to achieve successful surgical outcomes experience reduced long-term outcomes.