Motor imaging (MI) induces recovery and neuroplasticity in neurophysical regulation. However, a non-negligible portion of users presents insufficient coordination skills of sensorimotor cortex control. Assessments of the relationship between wakefulness and tasks states are conducted to foster neurophysiological and mechanistic interpretation in MI-related applications. Thus, to understand the organization of information processing, measures of functional connectivity are used. Also, models of neural network regression prediction are becoming popular, These intend to reduce the need for extracting features manually. However, predicting MI practicing’s neurophysiological inefficiency raises several problems, like enhancing network regression performance because of the overfitting risk. Here, to increase the prediction performance, we develop a deep network regression model that includes three procedures: leave-one-out cross-validation combined with Monte Carlo dropout layers, subject clustering of MI inefficiency, and transfer learning between neighboring runs. Validation is performed using functional connectivity predictors extracted from two electroencephalographic databases acquired in conditions close to real MI applications (150 users), resulting in a high prediction of pretraining desynchronization and initial training synchronization with adequate physiological interpretability.