This retrospective study compared two rehabilitation methods for patients who underwent a double-row surgical technique for Insertional Achilles Tendinopathy (IAT). Group 1 (G1) received traditional immobilization with casting and no weightbearing for six weeks, while Group 2 (G2) followed a modern functional rehabilitation program with early weightbearing in a walking boot. Data were analyzed from 63 patients (68 feet), with 48 patients (51 feet) in G1 and 17 patients (17 feet) in G2. The minimum follow-up was two years (mean of 32 months, ranging from two to nine years). Pre- and postoperative data, including VAS (Visual Analog Scale) pain scores and functional scores, were collected at six months and at the final follow-up. Additionally, return-to-work, driving, and sports data were evaluated. Pre- and post-VAS scores for G1 were 7.49/1.39 and for G2 were 7.8/2.2, showing no significant difference (p = 0.89). The overall mean VAS improved from 7.56 to 1.58 postoperatively. The FAAM-ADL score was 81.68 points (88.28 %), with men experiencing statistically greater improvements than women. Patients in G2 returned to work, driving, and sports faster within the first six months. Although G2 initially had slightly higher functional scores, no significant differences were observed between the two groups after six months. Early functional rehabilitation facilitated a quicker return to daily activities without increasing pain but did not provide better long-term functional outcomes compared to traditional immobilization. Thus, early weightbearing aids short-term recovery but does not enhance functional scores beyond six months.