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I'm reading Harry Potter for English study.

"Gryffindors have never gone so long without winning"

I think double negative means postive. So I think "Gryffindors have never gone so long without winning" means "Gryffindors have gone so long with winning".

But I heard that it means Gryffindors have been losing for a long time: their longest time ever.

Can you explain why???

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OP's example isn't what we normally mean by "double negation" in English (that's colloquial / uneducated usages such as He didn't do nothing wrong, where the two negatives don't "cancel each other out").

The cited example is just a straightforward literal usage. Gryffindors haven't won for a long time. So long, in fact, that they're currently experiencing their longest ever losing streak (extended period of losing / not winning).

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    There has never been a losing streak as long as this one
    – Smock
    Nov 22, 2019 at 14:37
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    Gryffindors have never had such a long losing streak [before]. Nov 22, 2019 at 14:53

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