Background and Aim: Despite the abundant literature, internal limiting membrane (ILM) peeling remains a controversial topic, especially in diabetic eyes. We compared the safety and effectiveness of intraoperative optical coherence tomography (iOCT)-assisted selective epiretinal membrane (ERM) peeling with dye-assisted ERM and ILM peeling, for the treatment of tractional diabetic macular edema (tDME). Material and Methods: In this single-center retrospective study, we evaluated consecutive patients with tDME who underwent iOCT-assisted selective ERM peeling (Group A) or “dual blue” dye-assisted ERM and ILM peeling (Group B). Best corrected visual acuity (BCVA) and central macular thickness (CMT) were compared over a 12-month follow-up. A linear mixed model analysis was performed. Results: At baseline, the two groups were comparable in terms of their demographic and clinical outcomes. No significant difference between BCVA and CMT was observed among the groups. Both groups showed significant improvement in outcomes at the last follow-up (p < 0.001), although only iOCT-assisted ERM peeling ensured significant visual gain and macular thinning (p < 0.001) one month after surgery. A significant effect of time on both outcomes (p < 0.001) and of time–treatment interaction on visual change (p = 0.02) were observed. In eight patients, macular edema recurred (Group A: two patients; Group B: six patients) and was managed with an intravitreal dexamethasone implant. In Group A, one patient developed a recurrence of ERM without the need for reoperation. Conclusions: iOCT-assisted ERM removal may be as effective as dye-assisted ERM and ILM peeling to treat tDME. Additionally, it ensures a quicker recovery of visual function and macular thickness. The observed ERM recurrence within the 1-year follow-up was mild and did not necessitate additional surgery.