Let them - if it helps them play the story they want to see for their characters then there's not a lot of problem with it. Having said that if the GM thinks a conflict should be a stinker they'll still end up facing hard resistances even when they recieved several complete failiures beforehand.
In my experience players can actually stack things in their character's favour far more easily by stacking up oodles of relevant modifiers from winning previous conflicts than they'd get for loosing a few.
Cheers,
Ash
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