Background: Previous studies have demonstrated several prognostic factors for retear after arthroscopic rotator cuff repair (ARCR). However, studies that histologically evaluate the quality of the torn rotator cuff (RC) tendon and its association with postoperative outcomes are limited. Purpose: To investigate factors associated with retear after ARCR using the suture bridge (SB) technique, including the degree of histological degeneration of the RC tendon edge. Study Design: Case-control study; Level of evidence, 3. Methods: The authors retrospectively evaluated 187 patients who underwent ARCR for full-thickness tears using the SB technique; intraoperative biopsy samples were taken to assess the degree of histological degeneration using the Bonar score. The cohort was divided into healed (n = 165) and retear (n = 22) groups according to magnetic resonance imaging results obtained ≥6 months postoperatively. The evaluation included preoperative patient data (age, sex, symptom duration, trauma history, history of heavy manual work, smoking habit, hypertension, diabetes mellitus, and hyperlipidemia) and radiological data (Hamada classification, Patte classification, Goutallier classification, and global fatty degeneration index [GFDI]). Additionally, intraoperative data (anteroposterior tear size, Lafosse classification for concomitant subscapularis tendon tear, and long head of biceps injury) and preoperative and postoperative clinical findings (active range of motion, University of California, Los Angeles [UCLA], score) were evaluated. Results: The retear rate was 11.8%. The retear group had a higher percentage of men (P = .031), higher Bonar score (P < .001), higher mean GFDI value (P = .002), higher rate of tear retraction degree (P = .010), and larger anteroposterior tear size (P = .020) than the healed group. The retear group had lower postoperative internal rotation (P = .031) and lower UCLA score (P < .001). Multivariate logistic regression analysis with a stepwise variable selection revealed anteroposterior tear size (odds ratio [OR], 2.4; 95% CI, 1.3-4.5; P = .004) and Bonar score (OR, 1.7; 95% CI, 1.3-2.4; P < .001) as independent predictors for a retear. Conclusion: The results indicate that end-stage severe tendon degeneration might affect retear. Therefore, further investigation on the progression mechanisms of tendon degeneration and development of methods to assess degenerative tissue might improve clinical outcomes after ARCR.