See, I feel like this is a case where they're putting the moment in the Hall of Fame, and the individual is just the one who gets the credit.
Forrest and Bonnar get in for having one of the most important fights and building the popularity of tUF, even though Forrest is the only one of those two who has an argument for getting in.
Serra's getting in for having the biggest upset in UFC history for years, referenced to this day. You can't argue it's not one of the most memorable moments in UFC history.
So I don't think of it as Matt Serra winning for his career, he's accepting the award on behalf of the moment.