YOU SAID:
i want the underdog to win
INTO JAPANESE
弱者が勝つことを望む
BACK INTO ENGLISH
I hope the weak will win
INTO JAPANESE
私は弱いが勝つことを望む
BACK INTO ENGLISH
I hope that the weak but win
INTO JAPANESE
私は弱いが勝つことを望む
BACK INTO ENGLISH
I hope that the weak but win
That didn't even make that much sense in English.