Salvage reconstruction of orbitomaxillary defects remains exceptionally difficult, particularly following prior free-flap failure, radiotherapy, and chronic infection. Successful restoration requires reliable vascularised bone for maxillary support, biologic reconstruction of the orbital floor, and well-vascularised soft tissue to re-establish oral–nasal separation and intraoral lining within a scarred and contaminated operative field. Virtual surgical planning was used to facilitate reconstruction with a fibula osteomyocutaneous free flap, allowing restoration of maxillary buttresses and alveolar architecture while providing soft tissue for palatal closure, intraoral lining, and midfacial contour. In this case, the fibula was harvested as a straight segment and osteotomised into a complex Z-shaped construct, a configuration that increases inset difficulty and places the vascular pedicle at risk of kinking, thereby challenging flap perfusion and survival. The osseous construct additionally provided stable inferior orbital rim support, enabling reconstruction of the orbital floor using an autologous iliac crest graft and avoiding reintroduction of alloplastic material into an infected field. This case highlights the feasibility of a single-stage salvage orbitomaxillary reconstruction using a multi-segment Z-shaped fibula osteomyocutaneous flap, emphasising the technical considerations required to maintain vascular integrity in complex osseous geometry. The approach is illustrated through a detailed case presentation and discussion of relevant technical considerations and existing literature.