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If the Hellmouth Cup was their coronation and the Toroidal Cup their collapse, the Klein Cup was purgatory for the San Francisco Boat Shoes . For over two decades, the Shoes existed in a state of perpetual, agonizing contention. While consistently hitting the top of the league in the regular season - often climbing to the very top of the pile - this sustained regular season performance translated to just one single hard-won Klein Cup trophy.

The Boat Shoes accumulated a staggering number of near-misses and soul-crushing playoff defeats, often at the hans of the same few rivals who became their white whales. The emotional resolve of Boat Shoes fans, which had been tested by the Donut Sickness in the Toroidal Cup and the seeming repeat in the Rainbow Cup, was temporary alleviated by the Taste of the Tenderloin beatdown during Rainbow/Season 24, but the Klein Cup was a trial by fire for true Shoes fans.