A Western Cape sailor, Alan Caldwell represents MAC in competitive dinghy racing. Alan's competitive record on SailingSA begins in April 2025. Since then 21 races across 2 regattas have been completed. Alan competes mainly in the Windsurfer LT fleet, alongside races in other fleets. Alan's best results include winning the SailingSA events in the multiple fleets fleet, as well as the SailingSA events in the multiple fleets fleet. Alan remains an active competitor in the Western Cape sailing circuit.