Background and objectives: In oral and maxillofacial operations, the iliac crest is a commonly used donor site from which to harvest bone for augmentation prior to dental implantation or for reconstruction of jaw defects caused by trauma or pathological lesions. In an aging society, the proportion of elderly patients undergoing iliac crest bone grafting for oral augmentation is growing. Although postoperative morbidity is usually moderate to low, the age and health of the patient should be considered as risk factors for complications and delayed mobilization after the operation. The aim of this retrospective study was to evaluate the postoperative morbidity and complications in elderly patients after the harvesting of iliac crest bone grafts for oral surgery. Material and Methods: Data were collected from a total of 486 patients (aged 7–85) who had a surgical procedure that included the harvesting of iliac crest bone grafts for intraoral transplantation. All patients were operated on between 2005 and 2021 in the Department for Oral and Maxillofacial Surgery of the University Hospital in Aachen, Germany. As parameters for postoperative morbidity and complications, gait disturbances, hypesthesia of cutaneous nerves, incision hernias, iliac crest fractures, delayed wound healing, and unfavorable scar formation at the donor site were all evaluated. Results: The study was performed with 485 patients due to the exclusion of one patient as the only one from whom grafts were taken from both sides. When younger and older patients were compared, neither gait disturbances (p = 0.420), nor hernias (p = 0.239), nor fractures (p = 0.239), nor hypesthesia (p = 0.297), nor wound healing delay (p = 0.294), nor scar problems (p = 0.586) were significantly different. However, the volume of the graft was significantly correlated with the duration of the hospital stay (ρ = 0.30; p < 0.01) but not with gait disturbances (ρ = 0.60; p = 0.597). Additionally, when controlling for age (p = 0.841), sex (p = 0.031), ASA class (p = 0.699), preexisting orthopedic handicaps (p = 0.9828), and the volume of the bone graft (p = 0.770), only male sex was associated with the likelihood of suffering gait disturbances (p = 0.031). Conclusions: In conclusion, harvesting bone grafts from the anterior iliac crest for intraoral augmentation is a safe procedure for both young and elderly patients. Although there is some postoperative morbidity, such as gait disturbances, hypesthesia, scar formation, or delayed wound healing at the donor site, rates for these minor complications are low and mostly of short duration. Major complications, such as fractures or incision hernias, are very rare. However, in our study, the volume of the bone graft was associated with a longer stay in hospital, and this should be considered in the planning of iliac crest bone graft procedures.