YOU SAID:
I don't know if they know that she knows about him
INTO JAPANESE
彼女が彼のことを知っていることを彼らが知っているかどうかはわかりません
BACK INTO ENGLISH
I don't know if they know she knows him
INTO JAPANESE
彼女が彼を知っていることを彼らが知っているかどうかはわかりません
BACK INTO ENGLISH
I don't know if they know she knows him
That didn't even make that much sense in English.