This chapter analyses the adoption of the Learning Grid for the development of challenging Application Scenarios in the eLearning domain. The Application Scenarios described in this chapter create a breakthrough in current learning practices. Instead of adopting a traditional information transfer paradigm, the proposed scenarios, in fact, promote and support a learning paradigm centred on the learner and focused on knowledge construction using experiential based and collaborative learning approaches in a contextualised, personalised and ubiquitous way. The purpose of our analysis is to understand and argue about the potential advantages of adopting the Learning Grid for the proposed scenarios. Preliminary findings show that Learning Grid can be considered an enabling technology for the presented scenarios since its features (e.g. dynamicity, adaptiveness, support for Virtual Organisation creation and management, advanced mechanisms for resources and services discovery on the basis of Quality of Services) are key to improve personalisation and knowledge construction in the learning process as well as communication and collaboration inside learning groups.