Fungal osteomyelitis (OM) is relatively rare. There is scarce literature discussing fungal OM in diabetic foot infections (DFIs). This case series explores the clinical characteristics of patients treated at a large tertiary academic center for DFI and found to have a causative agent of fungal origin in their bone on surgical intervention. Between July 2017 and March 2018, a prospective longitudinal analysis was performed of patients with diabetes admitted to our institution who underwent operative management of OM. Demographic, clinical, radiographic, and laboratory data were collected for all patients. Data between bacterial and fungal OM cohorts was analyzed for differences and similarities in patient characteristics and outcomes. All patients were followed 20 weeks postoperatively. Five patients with fungal OM were identified from the 35 cases where OM was confirmed through podiatric surgical intervention. In each fungal case, a Candida species was isolated from operative bone culture which included subspecies Candida albicans, C parapsilosis, and C glabrata. A P value ≥.05 was found in clinical characteristics between our cohorts. Wound healing was achieved in 40% of patients with fungal OM, and oral fluconazole successfully treated Candida OM in the cases that achieved healing. Diabetes can increase the risk of Candida OM. In DFIs, fungus can impede wound healing if not recognized and treated. Because Candida OM is typically indolent in nature, bone biopsy and mycological culture is recommended for definitive diagnosis and treatment.