Hey there @arthurashr - great question!

While Calendly won’t allow overlapping events in a single user account - there’s a workaround!

You can do this by adding additional users to your account, each of which will be a court. Then, create a team page and create an event type for each court so they can all be booked simultaneously. Each event type will need its own host - this will be the purpose of adding a user for each court (for example, five users). 

We have plenty of resources for you to learn about creating a team and setting up team events! The first step is adding your desired team members to your account from your Admin Management page. Then, you can set up a team page. Your team page will have all of your events specific to that team: round robin or collective. I suggest using a Round Robin event type for each court but assigning a single host so it’s a one-on-one. You cannot create a “true” one-on-one event on a team page, but this article goes over using a Round Robin or Collective instead:

If you'd like a more thorough breakdown of the team features, check out this recording that walks through the basics of using Calendly with your team. 

I hope this helps! Let us know if you have questions. =)

p.s. check out our New User Guide and our Company Admin Guide for help as you get started.