Hmm which way are you thinking it works because there's a wrong answer and since you're a Regina fan here to defend yourself I'm going to assume you chose the wrong answer...
But also since this is hypothetical they scheduled it to have tougher teams on their schedule like Regina does. Ain't that right?.....
That's also the point. Illustrating why should Highland play a team from a bigger city....like Iowa City? Same difference and again fwiw this Chicago team also has fewer students than Regina who is bigger than Highland.
Enjoy.
Good for Highland challenging them self. The things they learn in a game like that will help them get better. Similar to how Regina got better by competing with Solon and learning what they needed to do to get better while Solon was on their run. I am sure this is the 'wrong' answer and I eagerly await your big reveal to demonstrate your premise.