AbstractWe describe a class of combinatorial design problems which typically occur in professional sailing league competitions. We discuss connections to resolvable block designs and equitable coverings and to scheduling problems in operations research. We in particular give suitable boolean quadratic and integer linear optimization problem formulations, as well as further heuristics and restrictions, that can be used to solve sailing league problems in practice. We apply those techniques to three case studies obtained from real sailing leagues and compare the results with previously used tournament plans.