After tendon or ligament reconstruction, the interface between the hard bone and soft connective tissue is considerably weakened and is difficult to restore through healing. The tendon/ligament-bone interface is mechanically the weakest point under tensile loading and is often the source of various postoperative complications, such as bone resorption and graft laxity. A comprehensive understanding of the macro- and micro- features of the native tendon/ligament-bone interface would be beneficial for developing strategies for regenerating the tissue. This paper discusses the structural, biological and mechanical features of the tendon/ligament-bone interfaces and how these can be affected by aging and loading conditions. Impact Statement This review provides an up-to-date summary of the structural, biological and mechanical features of the tendon/ligament-bone interfaces, and how these can be affected by aging and loading conditions. A thorough understanding of these features provides critical foundation for developing advanced techniques for ligament/tendon reconstruction and soft-hard tissue interface engineering.