This study aimed to compare sub-Tenon’s and retrobulbar blocks during vitreoretinal surgery in terms of postoperative pain and surgeon experience. This prospective study included 53 patients scheduled for 23-gauge pars plana vitrectomy under local anesthesia. Patients were nonrandomly assigned to receive a xylocaine injection through either the transconjunctival sub-Tenon’s or retrobulbar routes, supplemented with intravenous (IV) sedation (midazolam + fentanyl). A sharp needle was used for both techniques. In the sub-Tenon’s group, anesthetic injection was initiated through subconjunctival administration after prepping and draping. Pain was assessed immediately postsurgery and the following day using a standardized questionnaire. Patient and surgeon satisfaction levels, along with complications in each group, were recorded. Of the 53 patients, 42 (79%) received the sub-Tenon’s block and 11 (21%) received the retrobulbar block. No statistically significant differences in pain scores, patient satisfaction, or surgeon satisfaction were found between the groups. Postoperative pain and surgeon satisfaction were negatively correlated in both groups (B = −0.465; P < 0.001), and a moderate-to-high correlation was observed between patient and surgeon satisfaction (B = 0.686; P < 0.001). Overall, sub-Tenon’s and retrobulbar blocks showed comparable effectiveness in terms of postoperative pain and patient and surgeon satisfaction in vitreoretinal surgery, with no significant differences in outcomes or complication rates.