Winsor Vraagom sails out of SBYC in the Western Cape. Winsor's earliest SailingSA result dates to October 2025. Since then 1 races across 1 regattas have been recorded. Winsor competes mainly in the Mirror fleet, alongside races in other fleets. Key performances include winning the SailingSA events in the multiple fleets fleet, along with the SailingSA events in the multiple fleets fleet. Winsor remains active in regional dinghy racing.