It really depends on what you mean by 'winning'. I would argue that in many cases 'winning' means keeping your head down and getting out alive at the other end with the necessary grades you need and the absolute minimum of effort along the way. To achieve that goal openly questioning authority is almost always counter productive. It's almost always better to either ignore authority, work around authority or work with authority than to challenge authority.

Sure you can be a PITA if you want, but unless you're the sort of person who loves being a PITA for its own reward (I was, to my shame), it probably won't get you anything meaningful.

Seconded. You can challenge authority without actually getting in trouble. It just requires having a modicum of legitimacy and reasonableness in your request. Having people skills can help too.

Many friends I know got through very well because they knew the rules of the game, and notably got some exceptional treatment because they made sure that they were taken seriously by the administration. One way not to do that is to be completely insufferable and unreasonably stubborn(which is how a lot of teenage kids act, granted).