Okay, so I'm a lawyer, but not a trademark lawyer (though I did take some intellectual property classes back in law school)...
The fact that the college is so small and not-well-known doesn't make their case weaker. It makes their case stronger. When you compare the Texas Rangers and the NY Rangers, both are well known brands in their own right, and it lessens the chance of confusion. But precisely because the College of Ste. Rose is not well known at all is what increases the chance for confusion.
I agree this seems likely to be settled, and I doubt it's in the millions of dollars. The only example I can think of is when the Winnipeg Jets came back into the league they deliberately borrowed from the RCAF roundel as their new symbol. In payment they signed an agreement with the Canadian Forces where the Jets would give $100k per year for ten years to military charities.