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Picking underdogs, unless you really believe in them, only really makes sense in bracket-type challenges, because then you benefit from being right for multiple rounds.
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There is some reasoning behind picking underdogs as they may perform better in certain surfaces or head to head against some players.
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True, plus there's the logic of pot-odds. If everyone is taking the favorite, then there's an advantage to taking the contrarian position.
It also starts making a lot of sense as a come-from-behind strategy.
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I will keep as it is for this contest. We need to abide by the rules. But I will review it for the next contest, probably lowering weight of initial rounds where is harder to see a surprising result and more likely to end up the match in 3 sets.