(1) Background: The current landscape of midface reconstruction is marked by ongoing evolution, with notable advancements in surgical techniques, microvascular procedures, and the implementation of multidisciplinary approaches, all of which have significantly enhanced both functional and aesthetic outcomes. Conventionally, microvascular anastomoses for free flaps in midfacial reconstruction have been executed using cervical vessels. However, this approach necessitates neck access, resulting in extraoral scars and a substantial pedicle length. In light of these considerations, using intraoral anastomoses via the facial vessels emerges as a promising alternative. This retrospective multicentric study aims to provide a comprehensive account of immediate midface reconstruction through intraoral anastomoses. (2) Methods: Between 2020 and 2023, patients were included who underwent intraoral resection of midface/orbit segments (Brown Classes I-VI) as a result of malignant diseases. In all cases, immediate reconstruction was accomplished by utilizing the facial vessels through an intraoral approach. Outcome criteria were identification of vessels, parotid duct or facial nerve damage, success of vascular anastomoses, and flap survival. (3) Results: A total of 117 patients with 132 flaps (91 osseous and 41 cutaneous) were included. The intraoral preparation of facial vessels was successfully completed in less than 1 h, and no complications related to the dissection or anastomoses were observed. In two cases, the vessel diameter was insufficient to facilitate anastomoses, necessitating adopting an extraoral approach. During a follow-up period of 48 months, two osseous flaps were lost, accounting for a 1.5% loss rate out of 132 flaps used. Additionally, 3 flaps experienced partial loss, including a skin island of a scapula, the border zone of a femur, and a rectus flap, resulting in a 2.3% partial loss rate out of 130 flaps utilized. (4) Conclusions: This case series underscores the feasibility of employing intraoral anastomoses for immediate complex midface reconstruction following oncological resection. This approach is particularly advantageous for flaps with shorter pedicles, as it helps mitigate external scarring and minimizes the risk of facial nerve injury.