Recent research highlighted the interest in 1) investigating the effect of variable practice on the dynamics of learning and 2) modeling the dynamics of motor skill learning to enhance understanding of individual pathways learners. Such modeling has not been suitable for predicting future performance, both in terms of retention and transfer to new tasks. The present study attempted to quantify, by means of a machine learning algorithm, the prediction of skill transfer for three practice conditions in a climbing task: constant practice (without any modifications applied during learning), imposed variable practice (with graded contextual modifications, i.e., the variants of the climbing route), and self-controlled variable practice (participants were given some control over their variant practice schedule). The proposed pipeline allowed us to measure the fitness of the test to the dataset, i.e., the ability of the dataset to be predictive of the skill transfer test. Behavioral data are difficult to model with statistical learning and tend to be 1) scarce (too modest data sample in comparison with the machine learning standards) and 2) flawed (data tend to contain voids in measurements). Despite these adversities, we were nevertheless able to develop a machine learning pipeline for behavioral data. The main findings demonstrate that the level of learning transfer varies, according to the type of practice that the dynamics pertain: we found that the self-controlled condition is more predictive of generalization ability in learners than the constant condition.