We present a comprehensive framework to assess these methods, considering the unique characteristics of financial data like non-stationarity, autocorrelation, and regime shifts. Through our analysis, we unveil the marked superiority of the Combinatorial Purged (CPCV) method in mitigating overfitting risks, outperforming traditional methods as evidenced by its lower Probability of Backtest Overfitting (PBO) and superior Deflated Sharpe Ratio (DSR) test statistic. Walk-Forward, by contrast, exhibits notable shortcomings in false discovery prevention, characterized by increased temporal variability and weaker stationarity. This contrasts with CPCV’s demonstrable stability and efficiency. We introduce novel variants of CPCV, including Bagged CPCV and Adaptive CPCV, which enhance robustness through ensemble approaches and dynamic adjustments based on market conditions. Our empirical validation using historical SP 500 data confirms these advanced cross-validation methods’ practical applicability and resilience. The analysis also suggests that choosing between Purged K-Fold and K-Fold necessitates caution due to their comparable performance and potential impact on the robustness of training data in out-of-sample testing. Our investigation utilizes a Synthetic Controlled Environment incorporating advanced models like the Heston Stochastic Volatility, Merton Jump Diffusion, and Drift-Burst Hypothesis alongside regime-switching models. This approach provides a nuanced simulation of market conditions, offering new insights into evaluating cross-validation techniques. We also address the computational aspects of these methods, demonstrating that parallelization significantly improves efficiency, making them feasible for large-scale financial datasets. Our study underscores the necessity of specialized validation methods in financial modeling, especially in the face of growing regulatory demands and complex market dynamics.