Sailing from SBYC, Winsor Vraagom competes in the Western Cape dinghy circuit. Winsor's earliest SailingSA result dates to October 2025. Since then 1 races across 1 regattas have been recorded. Winsor's primary class has been Mirror, with additional appearances in other fleets. Winsor's best results include winning the SailingSA events in the multiple fleets fleet, as well as the SailingSA events in the multiple fleets fleet. Winsor continues to compete regularly across provincial and national sailing events.