The Cronulla Shark Island Swim Challenge is an annual event of 2.3 km (1.4 mi), held at Cronulla Beach in Sydney, Australia.

The first Cronulla Shark Island Swim Challenge was held in October 1987. There was a medium swell and the water was choppy. There were only sixty-four competitors. The swim was 2.4 km (1.5 mi), from the beach shoreline out around Cronulla Point, around Shark Island and back to the beach. Long-distance swimmer David O'Brien was the inaugural winner.

• Official Swim Website
• Cronulla SLSC
• Cronulla SLSC
• Chris Dixon Photography