Management of acute and chronic pain after thoracic surgery for pulmonary resection or thymectomy remains a challenge for both thoracic surgeons and anesthesiologists. Advances in minimally invasive robotic procedures have made subcostal outside-the-cage (OTC) resections possible, but the procedure’s pain benefits have not been previously measured. A single-center cohort was consented to undergo robotic-assisted thoracoscopic surgery (RATS) with an OTC or transthoracic (TT) approach. On every post-operative day (POD), patients were asked to complete the visual analog scale (VAS) of pain, assigning a score of 0–10 with higher scores equaling higher pain intensity. Additionally, patients’ opioid consumption was recorded and classified using morphine equivalent dose (MED). Descriptive statistics of demographics, Mann–Whitney, and Chi-squared tests were performed in a matched analysis. Altogether, 50 OTC patients and 50 TT patients were included. For each group, 1 pneumonectomy, 19 lobectomies, 10 segmentectomies, and 20 thymectomies were performed. Between groups, most were male (n = 54; p = 0.42) and there were no differences in American Society of Anesthesiologists scores (p = 0.51), or tobacco consumption (p = 0.45). Patients who received an OTC approach experienced significantly lower pain scores on POD-0 (p = 0.001), POD-1 (p < 0.001), and POD-2 (p < 0.001). POD-3 OTC VAS scores were not different from those of the TT group (p = 0.09). Similarly, MED was lower for the OTC group on POD-0 (p < 0.001), POD-1 (p = 0.03), and POD-3 (p = 0.03). The RATS-OTC approach results in a more rapid decrease in self-reported pain by the patient as well as significantly lower levels of MED.