Background: Pediatric cutaneous hemangiomas (CHs) and vascular malformations (VMs) are common vascular anomalies requiring accurate differentiation for appropriate management. Ultrasonography (USG) and dermoscopy are non-invasive diagnostic tools that aid in their classification. This study evaluates the correlation between USG and dermoscopic findings in diagnosing these conditions. Methods: A retrospective cross-sectional study was conducted on 100 pediatric patients diagnosed with CHs or VMs at a tertiary care center. Demographic data, ultrasonographic features, and dermoscopic findings were analyzed. Histopathological confirmation was available for 40 cases. Sensitivity, specificity, and concordance between USG and dermoscopy were assessed. Results: The study population had a mean age of 2.8 ± 1.6 years, with 55% males and 45% females. Hemangiomas accounted for 64% of cases, while 36% were vascular malformations. USG findings showed 81.25% of hemangiomas as hypoechoic lesions with increased vascularity. VMs were categorized as low-flow (61.1%) or high-flow (38.9%). Dermoscopy of CHs revealed red-blue lacunae (75%) and white linear structures (34.4%), while VMs exhibited arborizing telangiectasias (50%) and blue/purple structures (58.3%). The USG-dermoscopy concordance rate was 86%, with 92.3% sensitivity and 88.1% specificity for CHs, and 85.7% sensitivity and 90.5% specificity for VMs. Conclusion: USG and dermoscopy provide a highly accurate, non-invasive approach for diagnosing pediatric vascular anomalies. Their combined use enhances diagnostic confidence, improving early identification and management of CHs and VMs.