I entered "Despite her winning, she is not happy", which DL corrected to "Despite she's winning, she is not happy". My answer might not be quite right, thanks to the subtle difference between "despite" and "although". However, "Despite she's winning" is just plain wrong! That's not valid English.
Despite is equivalent to "in spite of", which takes an object pronoun.
I write "Despite the fact that she is winning, she is not happy", which was marked incorrect. While I understand that although is a better direct translation (word-for-word), I usually use the phase "despite the fact that" in place of "although". This phrase also helps me remember the "-ש" that comes with the phrase. Does that substitution make sense to anyone? Is there a more strict difference between "despite" and "although" in Hebrew than there is in English?
I think that the problem was inserting the word "fact". I know that that is the actual phrase in English, but computer translators are not good with phrases. But even so, I've seen it translated as למרות העובדה. Or maybe the problem is that after "despite" you need a noun and since there is a verb here, "even though" is set as the correct answer.
למרות - lamroth ( although)
שהיא (that she)