This paper presents the decision support system that has been defined and developed under the umbrella of the NESTORE project. The main goal of the proposed system is to help users in selecting coaching plans by proposing personalised recommendations based on their behaviours and preferences. Recognising such behaviours and their evolution over time is therefore a crucial element for tailoring the interaction of the system with the user. A three-layer system composed of pathways, coaching activity plans, and coaching events, constitutes the so-called coaching timeline on which the analysis is grounded. Various techniques are used to model and personalise the recommendations and feedback. Firstly, the indicators are extracted from disparate data sources, then these are modelled through a profiling system and, finally, recommendations on the pathways and coaching plans are performed through a scoring and a tagging system.