Background: Delamination of cuff tendons has a negative impact on outcomes following arthroscopic rotator cuff repair (RCR). The purpose of this study is to compare en masse repair (EMR) and separate double-layer repair (SDLR) for delaminated rotator cuff tears. Methods: A systematic literature search was conducted on major databases (MEDLINE/PubMed, EMBASE, Cochrane Library, and Scopus) until 1 June 2023. Comparative studies with a minimum 24-month follow-up of patients undergoing arthroscopic RCR for delaminated tears were included. The outcomes assessed retear rates and functional outcomes. Results: Five eligible studies involving 325 cases were analyzed. The meta-analysis showed no significant difference in retear rates between SDLR and EMR for delaminated tears (OR = 0.73, 95% CI: 0.35–1.49). However, the meta-analysis demonstrated a significant intergroup difference in favor of the SDLR for the total Constant score (SMD = 0.68, 95% CI: 0.35 to 1.02), SST score (SMD = 0.37, 95% CI: 0.02 to 0.71), and postoperative range of abduction (SMD = 0.34, 95% CI: 0.03 to 0.64). Conclusion: The evidence suggests that the SDLR in arthroscopic RCR for delaminated rotator cuff tears leads to improved short-term functional outcomes and range of motion compared to EMR. However, there is no significant difference in retear risk between the two approaches.