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ABSTRACT Two boats sailing in close proximity may inevitably compare their boat speeds, perhaps even "race" each other. Over the last few centuries there have been numerous handicap systems designed to estimate the performance of different boats relative to one another. Corollary to handicapping is another arcane art, that of scoring races. Scoring methods have both technical options, in part determined by handicap rules, as well as "human engineering" options in the sense that different solutions can work best for different constituencies, be they race organizers or sailors. Options may include single vs. multiple ratings, time on distance vs. time on time, pre/during/post race handicapping, attempts to predict the environmental conditions on the race course, constructed courses, pursuit vs. staggered vs. fleet start racing, and performance curve scoring. The underlying assumptions and motivations for these choices are presented along with the consequences of adopting them. The expectations of the competitors, and indeed their ability to intuitively grasp the fundamentals of how elapsed times are transformed into race rankings, are discussed with a view towards finding solutions that achieve a successful balance of fairness, transparency and acceptance. INTRODUCTION The methods available to scoring sailboat races are entirely dependent on the methods with which sailboats themselves are handicapped or rated. The two terms "handicap" and "rating" are often used interchangeably and may imply different concepts to different folks. In this paper both refer to the generation of time allowances that are applied to boats elapsed times to "allow" a slower to boat to compete against a faster one, hopefully with something close to competitive parity. This paper refers to handicap/rating systems only to the extent that they influence scoring options. Early Approaches to Scoring Length, the apparent size of a boat, was a reasonable approach to assigning time allowances in that there is some validity to the concept that "bigger is faster." In fact an effective boat length was used to generate handicaps. There is a technical basis for using length to determine boat speed.