During the recent years, several new Information and Communication Technology solutions have been developed in order to meet the increasing needs of elderly with cognitive impairments and support their autonomous living. Most of these solutions follow a human-centred paradigm that aims to provide users with personalised services according to their needs by also ensuring their safety with mechanisms that can automatically trigger appropriate actions in situations where there may be a risk for an elderly. The present paper presents a hybrid matchmaking approach that uses efficiently both a rule-based and a statistical matchmaker in order to (a) propose ambient assisted living services to the end-users, based on their role, status and context of use and (b) identify and resolve problematic cases by automatically selecting the most proper set of services to be called in a single or combined manner.