Background: Parietal pain is often associated with the port site entry used during laparoscopic cholecystectomy. Objectives: To determine the effects of bupivacaine infiltration to the port sites after laparoscopic cholecystectomy on postoperative pain intensity (assessed using visual analogue scale) and need for rescue analgesia. Materials and Methods: This was a hospital based, prospective, triple blinded, randomized controlled trial conducted in the Department of General Surgery, Chettinad Academy of Research and Education, Chennai, India between January, and April 2024 among patients undergoing elective laparoscopic cholecystectomy. Results: A total of 60 patients were included – 30 in Group A receiving 10ml solution of 0.25% bupivacaine through the port site (local infiltration) at the end of the surgery before sound closure, using 2.5ml at each port site, and 30 in Group B, the control group not receiving local infiltration (or intra-incisional; port site) of bupivacaine. The baseline characteristics of the two study groups (including age, gender, body mass index (BMI), and duration of surgery) were comparable. Comparing the need for rescue analgesia, 13.3% patients in Group A and 46.7% patients in Group B required rescue analgesia – the difference in need for rescue analgesia between was found to be statistically significant (p<0.05). The mean (SD) duration of hospital stay in Group A was 1.6 days (0.3) and that in Group B was 2.3 days (0.5) – the difference in duration of hospital stay was found to be statistically significant (p<0.05). The mean (SD) visual analogue scale scores were significantly (p<0.05) lower in Group A in comparison with Group B at 1 hour (8.8 (0.7) vs 9.6 (0.9)), 2 hours (6.4 (0.4) vs 6.9 (0.5)), 4 hours (4.9 (0.7) vs 5.4 (0.3)), 6 hours (3.1 (0.6) vs 3.4 (0.4)), and at 8 hours (2.3 (0.5) vs 3.3 (0.8)). Conclusion: Implementing bupivacaine infiltration at port sites can be a simple, effective, and low-cost strategy to enhance postoperative pain management.