Right now, it seems like replacement prizes for repeat event winners is at each individual staff member's discretion and it's pretty confusing. For example, Slacky is known to give replacement hats to people who win an event if they already have the prize hat. However, Mashboyellis won't. It's not a matter of which is right or wrong, because that's all opinion, it's just that this variance does nothing but create problematic situations.
There are also staff members who will replace your hat one day, but then not others. Then, some of the staff who won't replace your hat will sometimes give you a cookie and others won't. It's just 20 different variables when it should be a universal yes or no, for the purpose of clarity and fairness.

I've personally tried my best to keep track of who will or won't give a replacement prize:
I sort of gave up though, because someone told me that Dual has given them a replacement hat before.

Can we get an established rule on this for staff to follow? Sometimes, I'll be in an event like Bush Race or Hidden Paths and I'll have no idea if I'll get a replacement hat or not. If I can't, I don't want to touch the trophy and win the event because I get nothing out of it.