The study aimed to identify factors affecting the management and prognosis of iatrogenic cervical oesophageal and hypopharyngeal perforations (iCEHPs). We retrospectively analysed 24 patients treated for iCEHP between 2004 and 2021 at a tertiary university medical centre. Data on demographics, clinical features, imaging, management and outcomes were collected. Factors associated with primary management and patient outcome were assessed. The most common management approach was surgical neck exploration (15 patients, 62.5%). Surgical management was used in 93% of uncontained perforations compared to 11% of contained perforations (p < 0.001). Surgically-treated patients had higher levels of C-reactive protein (CRP) than conservatively-treated patients (median, 18.3 vs 4.8 mg/dL; p = 0.001). Delayed diagnosis (≥ 24 hours) was associated with increased mortality (100 vs 5%; p = 0.011). The mortality rate was significantly higher in patients who had a history of neck irradiation than in patients who did not (67 vs 5%; p = 0.032). Early diagnosis of iCEHP improves outcomes. The appropriate management should be carefully selected on the basis of CRP level and imaging findings. Prior neck radiation is a poor prognostic factor.