Background Gastrointestinal perforation due to foreign body ingestion is rare, comprising less than 1% of cases. Despite their sharp shapes, perforation from fishbones is even rarer, with the ileum as the most common site. Clinically unsuspected accidental fishbone injections can be challenging to diagnose with non-specific clinical manifestations. Method This is a single patient with two cases completed at a metropolitan tertiary hospital. Result A 46-year-old male presented with a four-day history of acute migratory right iliac fossa pain and constipation for two days. He had a history of fishbone-induced distal ileal perforation two years ago, requiring open small bowel resection and removal of a fishbone. He had no significant comorbidities, and vital signs were normal. Examination revealed a distended abdomen with localised peritonism in the right lower quadrant. Blood tests indicated elevated inflammatory markers (WCC of 11.2 × 109/L, CRP of 108 mg/L). An abdominal CT scan showed a suspected fishbone-induced perforation in the distal ileum, with no signs of appendicitis or obstruction. An urgent laparotomy confirmed a fishbone and perforation at the previous side-to-side anastomosis, leading to small bowel resection and primary anastomosis. Histology revealed a mesenteric abscess and acute serositis with no malignancy. The post-operative course was unremarkable, and he was discharged on day seven of admission. Conclusion To our knowledge, this is the first report of repeated small bowel perforations caused by fishbone ingestion. Fishbone perforation is uncommon, and diagnosis can be challenging. Timely diagnosis with CT and surgical intervention is essential to prevent complications and enhance patient outcomes.