Background: While patient age, tear size, and muscle fatty infiltration are factors known to affect the rate of tendon healing after rotator cuff repair, the effect of tendon delamination is less known. Purpose: To assess the effect of tendon delamination on rotator cuff healing after arthroscopic single-row (SR) repair. Study Design: Cohort study; Level of evidence, 3. Methods: Consecutive patients (N = 117) with chronic full-thickness rotator cuff tears underwent arthroscopic SR repair with the tension-band cuff repair. The mean ± SD age at the time of surgery was 60 ± 8 years. There were 25 small, 63 medium, and 29 large tears. Tendon delamination was assessed intraoperatively under arthroscopy with the arthroscope placed in the lateral portal. Patients were divided into 2 groups: those with nondelaminated (n = 80) and delaminated (n = 37) cuff tears. The 2 groups were comparable for age, sex, body mass index, preoperative pain, strength, and a Constant-Murley score. Repair integrity was evaluated with sonography (mean, 24 months after surgery; range, 6-62 months) and classified into 3 categories: type A, indicating complete, homogeneous, and thick coverage of the footprint; type B, partial coverage with a thin tendon; and type C, no coverage of the footprint. Results: The prevalence of tendon delamination observed under arthroscopy was 32% (37 of 117), which increased with tear size and retraction: from 15% in small tears to 32% in medium tears and 45% in large tears (P = .028). Postoperatively, 83 patients had complete coverage of footprint (type A = 71%) and the cuff was considered healed, whereas 26 had partial coverage or a thin tendon (type B = 22%) and 8 had no coverage (type C = 7%). Overall, the rate of complete healing was 78% in nondelaminated cuff tears and 57% in the case of tendon delamination (P = .029). In large retracted tears, the healing rate dropped from 81% in the absence of delamination to 39% when the tendons were delaminated (P = .027). Conclusion: Tendon delamination increases with tear size and retraction. Patients with chronic delaminated and retracted rotator cuff tears (stage 2 or 3) are at risk of failure after SR cuff repair, whereas patients with small delaminated rotator cuff tears (stage 1) involving only the supraspinatus can be treated with an SR cuff repair with a high chance of tendon healing. These results suggest that SR cuff repair may be insufficient to treat delaminated chronic cuff tears. To improve the anatomic outcomes of rotator cuff repairs, surgeons should consider treating delaminated tears with a double-row or double-layer repair.