Mesoporous bioactive glasses (MBGs) associated with an anti-osteoporotic drug (ipriflavone) have been prepared. With this aim, MBGs were functionalised with different organic groups by following a post-grafting method, thus retaining the mesoporous network of the bioactive substrates. Drug-delivery tests were carried out by using ipriflavone as a hydrophobic model drug. Our results revealed that by means of the proper functionalisation, most of the drug is retained in the mesoporous network. By tailoring the hydrophobicity of the surface with functional groups, the drug–material link can be tuned, thereby ensuring the long-term delivery of ipriflavone. In vitro bioactive tests demonstrate that these systems exhibit the same excellent behaviour of non-functionalised MBGs. The possibility to add a bone resorption inhibitor such as ipriflavone to highly bioactive materials confirms functionalised MBGs as very promising bone-tissue regeneration systems.