The history of bone flaps in reconstructive surgery is a journey spanning centuries. It began around 2000 BC when Peruvian monks used metal plates to correct trepanation errors. In 1668, a Russian surgeon used a canine bone graft to repair a skull defect, albeit facing religious backlash due to xenograft use. The nineteenth century saw experimentation with autologous and allogeneic nonvascularized bone grafts, highlighting the importance of blood flow in bone healing. Recognition grew that maintaining blood supply and using autologous sources were crucial for structural integrity. Autologous vascularized bone transfer advanced alongside other surgical techniques, leading to better healing rates, resistance to resorption, and biomechanically superior results. The history of bone supply research dates back to Antoni van Leeuwenhoek in 1674, who described Haversian canals’ role in nutrient supply. In the eighteenth century, Bernhard Albinus identified finer blood vessels in bone. However, bone was considered inert for reconstruction in the nineteenth century. Pedicled vascularized bone transfers gained momentum with Wilhelm Wagner’s osteoplastic flap in 1889, offering access to the cranial vault. Other surgeons followed suit for various defects, especially when nonvascularized grafts failed. World War I prompted facial reconstruction innovations, but practical limitations hindered prelamination and pedicled bone graft use. Antiseptic practices and penicillin supported nonvascularized bone grafts in the early twentieth century. The study of bone blood supply’s patterns became critical for free vascularized bone transfer. Joseph Trueta, Henry Crock, and Murray Brookes contributed to understanding blood flow in cortical bone, showing the importance of periosteal and endosteal systems. Microsurgery opened new avenues, with tissue engineering and 3D-printed scaffolds enhancing bone reconstruction. Vascularized bone transfer gained importance in composite defects and critical bone reconstructions. Incorporating vascularized bone marrow has introduced donor-specific tolerance with mixed chimerism. Today, free vascularized bone transfer is a preferred method for critical bone defects, representing the culmination of centuries of surgical evolution in maintaining blood supply for successful bone healing.