This investigation sought to assess how oral and maxillofacial surgery (OMS) specialists and trainees understand, perceive, and apply artificial intelligence (AI) in their clinical work and training. A cross-sectional questionnaire was distributed to OMS clinicians and residents in Singapore to gather their perspectives on AI in the field. The instrument contained 25 items across five sections and was administered through an online survey system. A total of 48 individuals responded, comprising 37 specialists and 11 trainees. Among them, 60.4% indicated they lacked strong knowledge of AI, 52.1% were unfamiliar with AI applications in OMS, and 81.3% had never received formal instruction related to AI. Many believed that AI could support diagnostic and treatment-planning tasks (72.9%) and help improve patient outcomes (75.0%), and also agreed that AI should be integrated into OMS training (68.8%). No gender-associated differences were observed, although younger clinicians showed more positive views (p < 0.05). Key concerns included potential diagnostic or planning errors (77.1%), excessive reliance (70.8%), data security or privacy issues (41.7%), and rising healthcare expenses (41.7%). Despite 68.8% using AI in everyday activities and 62.5% noting that AI made tasks easier, most had not adopted AI in clinical work (62.5%) and felt insufficiently trained or resourced to do so (79.2% and 58.3%, respectively). OMS clinicians and trainees in Singapore generally express positive expectations regarding AI, with younger participants showing greater enthusiasm. Nonetheless, both familiarity and actual utilization of AI remain limited.