We consider the problem of analyzing the probabilistic performance of first-order methods when solving convex optimization problems drawn from an unknown distribution only accessible through samples. By combining performance estimation and Wasserstein distributionally robust optimization, we formulate the analysis as a tractable conic program. Our approach unifies worst-case and average-case analyses by incorporating data-driven information from the observed convergence of first-order methods on a limited number of problem instances. This yields probabilistic, data-driven performance guarantees in terms of the expectation or conditional value-at-risk of the selected performance metric. Experiments on convex quadratic minimization and Lasso show that our method significantly reduces the conservatism of classical worst-case bounds and narrows the gap between theoretical and empirical performance.