Advances in drug delivery systems adapted with regenerative medicine have transformed healthcare by introducing innovative strategies to treat (and repair in many instances) disease-impacted regions of the human body. This review provides a comprehensive analysis of the latest developments and challenges in integrating drug delivery technologies with regenerative medicine. Recent advances in drug delivery technologies, including the design of biomaterials, localized delivery techniques, and controlled release systems guided by mathematical models, are explored to illustrate their role in enhancing therapeutic precision and efficacy. Additionally, regenerative medicine approaches are analyzed, with a focus on extracellular matrix components, stem cell-based therapies, and emerging strategies for organ regeneration in both soft and hard tissue and in vitro model engineering. In particular, the review also discusses the applications of cellular components, including stem cells, immune cells, endothelial cells, and specialized cells such as chondrocytes and osteoblasts, and highlights advancements in cell delivery methods and cell-cell interaction modulation. In addition, future directions and pivotal trends emphasizing the importance of interdisciplinary collaboration and cutting-edge innovations are provided to address successful therapeutic outcomes in regenerative medicine.