Sailing from HYC, Roger Sherriff competes in the Western Cape dinghy circuit. Since February 2025, 30 races across 5 regattas have been recorded for Roger. Most of Roger's racing has been in Hobie 16, with additional starts in other fleets. Highlights include winning the 2026 HYC Cape Classic in the Hobie 16 fleet, along with the 2025 HYC Cape Classic Hobie 16 in the Hobie 16 fleet. Roger remains active in regional dinghy racing.