Background/Objectives: Postoperative sensitivity remains a common challenge following direct composite restorations, especially in Class II cavities with deep proximal boxes. The snow-plow and resin-coating techniques have been proposed to improve marginal adaptation and reduce postoperative discomfort; however, comparative clinical data remain limited. This prospective, split-mouth, quasi-experimental study aimed to compare postoperative pain associated with Class II restorations placed using either the snow-plow or resin-coating technique. Methods: This prospective, split-mouth study followed 83 adult patients (aged 18–45 years) who received bilateral Class II composite restorations for one week. The study received ethical approval. Each participant received one restoration using the snow-plow technique and another using the resin-coating approach. Pain intensity was evaluated using a 10-point visual analog scale (VAS) at baseline, 24-h, 72-h, and 1-week postoperatively. Analyses included Wilcoxon signed-rank, Friedman, Chi-square, McNemar, and two-way repeated-measures ANOVA tests. Results: Pain intensity peaked at 24-h for both techniques and declined significantly by 72-h and 1 week (p < 0.001). The snow-plow technique showed slightly lower mean pain scores at 24 and 72 h (p = 0.026 and p = 0.004, respectively), though categorical analyses revealed no significant difference in pain-free or minimal-pain proportions at any interval (p > 0.05). Both techniques showed significant within-group reductions in pain over time (p < 0.001). Conclusions: Both restorative approaches demonstrated similar postoperative pain trajectories, with substantial improvement by one week. While minor differences in early mean pain intensity were observed, these were not clinically significant. The findings suggest that either technique can be effectively employed to achieve satisfactory postoperative comfort when modern adhesive protocols are applied. Clinicians can therefore select either technique based on preference and clinical circumstances, with the expectation of comparable short-term postoperative comfort outcomes.​