Yeah, draw, considering they'd both score perfects.
"To all visitors from Transylvania looking for the head of Voivode Dracula: Yes, we have it. Yes, he's dead. No, you cannot see it. No, he will not return and invade you again. It has been over thirty years, please stop pestering us."
Will Hunting, in case if there is something yet to be solved in math being listed in the competition.
There is an episode out of the early seasons of TBBT where Sheldon enteres a Physics Bowl and he participates against his own friends who are the rest of the gang in the show. At the end of the show he lost to his friends because he didn't know the answer to the last question and he refuesed to listen to a member of his own team who has the answer. (A cleaner who was once a Physicist in former USSR)
It is in the character setting of Sheldon that he can't solve everything even in his own field. Will Hunting on the other hand, has no such limit in his setting under academia. As the plot in his movie was kicked started by him solving math problem that professors in that field can not. A field which he IS NOT specialised in and
Also Will Hunting is not a follower when it comes to solving problem. Sheldon on the other hand is, and it takes him 2-3 sleepless days of non-hardwork to realise electron travels as a wave rather than particle. It happened to Sheldon by luck, rahter than brilliance in front of the white board. Sheldon has problem with practical engineering, but Will Hunting can use tools in construction and automotive engineering.
If it's a question of who is smarter, probably Will. Sheldon does seem to get outmatched or stumped at times while Will solves like an absurdly difficult proof (well, what was supposed to be one within the confines of the story) that a world renowned Fields Medalists took decades to figure out casually while working as a janitor.