Handlebar injuries are a common mechanism of blunt abdominal trauma in the paediatric population. Although external signs may appear minor, significant intra-abdominal injuries can occur. A large paediatric case series found that 6% of handlebar injuries involved bowel or mesenteric trauma. Early clinical assessment is often falsely reassuring, and delayed presentation is well recognised. We present the case of a 15-year-old male who sustained a high-speed handlebar injury. He initially presented on Day 10 post-injury with abdominal pain, vomiting, and a visible handlebar sign. CT demonstrated small bowel dilatation with a single transition point. He improved with conservative management and was discharged. On Day 26, he re-presented with worsening symptoms. MRI showed persistent small bowel dilatation, and diagnostic laparoscopy identified a short mid-jejunal stricture with mesenteric scarring. A small bowel resection with stapled side-to-side anastomosis was performed. He re-presented one day after discharge (Day 39) with recurrent pain and vomiting. MRI confirmed a high-grade small bowel obstruction. Laparotomy revealed an omental band adherent to the anastomotic staple line, encircling the distal bowel. The band was divided, and the patient recovered well. This case highlights the diagnostic challenges associated with handlebar injuries. Cross-sectional imaging in children requires careful consideration due to radiation exposure, and no standardised imaging or follow-up protocols exist. The role of biomarkers remains inconclusive. A high index of suspicion should be maintained even with delayed presentation or reassuring initial findings. Serial clinical assessments, early repeat imaging for persistent symptoms, and clear discharge safety-netting are essential. Delayed small bowel obstruction may occur weeks after injury, underscoring the need for vigilance.