In a world where the data is a central piece, we provide a novel technique to design training plans for road cyclists. This study exposes an in-depth review of a virtual coach based on state-of-the-art artificial intelligence techniques to schedule road cycling training sessions. Together with a dozen of road cycling participants’ training data, we were able to create and verify an e-coach dedicated to any level of road cyclists. The system can provide near-human coaching advice on the training of cycling athletes based on their past capabilities. In this case study, we extend the tests of our empirical research project and analyze the results provided by experts. Results of the conducted experiments show that the computational intelligence of our system can compete with human coaches at training planification. In this case study, we evaluate the system we previously developed and provide new insights and paths of amelioration for systems based on artificial intelligence for athletes. We observe that our system performs equal or better than the control training plans in 14 and 24 week training periods where it was evaluated as better in 4 of our 5 test components. We also report a higher statistical difference in the results of the experts’ evaluations between the control and virtual coach training plan (24 weeks; training load: X2 = 4.751; resting time quantity: X2 = 3.040; resting time distance: X2 = 2.550; efficiency: X2 = 2.142).