Aims: Infantile haemangiomas (IH) are the most common tumour of infancy. While propranolol has been established as the gold standard treatment, the natural history and optimal management for IH affecting the airway, including treatment duration and risk of rebound symptoms remains poorly defined. This study aimed to assess the natural history and management of upper airway IH in the propranolol era. Methodology: A retrospective cohort review was conducted across a 10-year period (January 2014–December 2023) at a single quaternary paediatric referral centre. The study included all patients diagnosed with IH affecting the trachea, larynx, pharynx, or nasal/oral cavities. Data on demographics, site and sequalae of disease, treatment regimen, duration, adjuvant treatment were collected for analysis by three independent investigators. Descriptive analysis was performed and where sufficient data allowed, inferential analysis was performed using Wilcoxon signed-rank tests, Fisher’s exact test, Spearman correlation analysis and logistic regression to analyse the efficacy of propranolol, efficacy of adjunct treatment and relationship between treatment duration and clinical outcomes. Results: A total of 28 patients with upper airway IH were identified. Upper airway IH presented at a median age of 3 months and required intervention with propranolol in 24/28 (86%) of cases. Median propranolol treatment duration for upper airway IH was 13.1 months. Overall incidence of rebound symptoms following treatment cessation was 7/28 (25%), with oropharyngeal lesions demonstrating the highest risk. Significant functional stigmata, primarily altered breathing or cosmetic deformity, were recorded in 12/28 (43%) and 10/28 (36%) of the upper airway cohort, respectively. Conclusion: Upper airway IH represent a distinct, high-risk subset of vascular tumours requiring aggressive management compared to cutaneous IH. These findings underscore the need for prolonged propranolol courses and surveillance.