INTRODUCTION: Congenital diaphragmatic hernia (CDH) most commonly seen on the left side, presenting usually in neonates and infants with respiratory distress. IMPORTANCE: CDH presenting as tension hydropneumothorax requiring urgent intercostal chest tube drainage (ICD) and subsequently inducing the injury to the herniated bowel and lung, is not an uncommon event, rarely reported in toddlers as well as its management. CASE PRESENTATION: Two such rare cases of CDH presenting with tension hydropneumothorax requiring ICD insertion and their consequences have been discussed here. CLINICAL DISCUSSION: CDH can present later in life due to consequent recurrent bronchopneumonia and failure to thrive. CONCLUSION: Clinical history and clinical judgement can only aid the surgeon in avoiding such confusing clinical scenarios.