It shouldn't happen, that bug was reported for several times already. We'll try to see what causes this.
Thanks for reporting.
There's no audio for this sentence (it wasn't recorded), by pronunciation seems to be: Lamrót sahí menatséakhet, hi lo simkhá, but I'm not sure.
I don't know enough to correct the rest but היא is probably better transliterated as he not hi. Actually a somewhat useful way to remember the word, that she is he in hebrew. (Or the saying who is he, he is she.)
למרות - lamroth ( although)
שהיא (that she)
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.