The Winograd technique is a common surgical treatment for ingrown toenails. Attempting to improve the results of this technique, two modifications were adopted: the incisional approach and the use of adhesive approximation strips. This study aimed to compare the conventional technique and the modified version based on (i) postoperative complications, (ii) healing time, (iii) recurrence rate, and (iv) overall patient satisfaction. A longitudinal, observational, and retrospective design was used, with a sample of 208 patients divided into the modified Winograd technique (n = 111) and the conventional Winograd technique (n = 97) in three clinics in Portugal, with follow-up periods of more than 15 years and 10 years, respectively. The modifications to the Winograd technique revealed fewer postsurgical complications, in terms of infections (1.8% vs. 20.62%, p < 0.010), recurrence rate (2.7% vs. 5.21%, p > 0.05), shorter recovery time (8.10 ± 0.76 vs. 14.51 ± 3.48 days, p < 0.001), and lower postoperative pain and better satisfaction with the functional and esthetic results, with the patient’s overall satisfaction, and with significant differences in relation to the conventional technique (p < 0.001). The modifications performed showed a lower rate of infection, decreased healing time, and better patient satisfaction, suggesting that it may be adopted in clinical practice for the treatment of stages II and III ingrown toenails.