The maxillary canine is the second most commonly impacted tooth after the maxillary third molar. Identifying risk factors for impaction is crucial for timely intervention; panoramic radiographs are particularly valuable for screening and identification purposes. This study aims to explore the association between transverse maxillary deficiency with bilateral crossbite, and the risk of maxillary canine impaction. A cross-sectional retrospective study was conducted on records of pediatric patients (7–13 years old) undergoing orthodontic evaluations. Panoramic radiographs were analyzed to assess the risk of canine impaction using the sectorial method, distance from the occlusal plane, and the alpha angle. Results from 48 canines of patients with transverse maxillary deficiency and bilateral crossbite were compared to canines of sex- and age-matched patients without these malocclusions. Statistical analysis was performed by the Shapiro–Wilk test, Levene’s test, or a t-test. There were no significant differences in high-risk canine impaction between groups when considering sector classification or distance from the occlusal plane. However, the control group showed a significantly higher risk according to the alpha angle (≥25°). No overall significant difference in risk was observed, suggesting that transverse maxillary deficiency with bilateral crossbite may not increase the risk of maxillary canine impaction.