You can do it on the site now.
1. Go to Add Data->Add Coach to add all the coaches if they aren't in the system
2. Go to Information->Team History and search your team
2a. Update team history that is there.
Note that it will be years in which a school won a sectional, regional, etc title.
3. Then go to Add Data->Add Team History and add the history that is not already there
Then have a beverage of your choice and check your team's profile page in case you missed or duplicated years. As soon as an item is added it will update your page.