Introduction Non-syndromic oral clefts, affecting one in 700 newborns in India, are the most prevalent craniofacial anomalies, with genetic or environmental causes impacting various life aspects. Studies indicate higher dental disturbances, particularly impacted canines, in cleft lip and palate (CLP) patients compared to non-cleft individuals. Impacted canines, trapped by hard tissues, require early diagnosis to prevent orthodontic issues. The widely used Ericson and Kurol method employs orthopantomograms (OPGs) to classify canine impaction in typical children. However, diagnosing canines in CLP patients is challenging due to palate defects and post-grafting complications. This study aims to compare the utility of the Kumar and Daigavane (KD) grading system and the sector classification to determine the best method for diagnosing impacted canine eruption paths. Method This cross-sectional comparative observational study was conducted at Sharad Pawar Dental College's Department of Orthodontics and Dentofacial Orthopaedics. The sample size, calculated using a significance level of 5% and a prevalence of 1%, required a minimum of 16 participants aged 9-11 years with non-syndromic clefts and impacted canines. Patients with systemic diseases or over 12 years of age were excluded. The sectoral and KD classification systems collected and evaluated OPGs from qualifying cleft patients. Sector classification considered the angle between the occlusal plane or canine tip and the adjacent tooth's long axis, while KD's classification considered the Frankfort horizontal plane, occlusal plane, vertical height from the occlusal plane, canine apex root position, and canine exposure to the cleft defect. Results The study found an 81.25% agreement between the KD grading system and the sector classification, with a Cohen's kappa value of 0.586, indicating a moderate agreement. The KD system showed 81.82% sensitivity and 80.00% specificity, with positive and negative predictive values of 90.00% and 66.67%, respectively. The receiver operating characteristic (ROC) curve analysis revealed the KD system's superior performance in identifying impacted and non-impacted canines compared to the sector classification. Conclusion The KD grading system demonstrated higher efficacy than the sector classification for evaluating the impacted canines in children with unilateral cleft lip and palate (UCLP). The KD system's high sensitivity and specificity make it a valuable tool for predicting canine eruption paths and addressing anatomical challenges in cleft conditions. This study highlights the need for accurate diagnostic tools tailored to cleft patients and contributes to advancing orthodontic treatment outcomes through improved classification systems.