Legacy Desktop Program

As of December 1st, 2021, the legacy Desktop program is no longer available for download as Diamond Scheduler transitions to be a new, web-based platform.

Please see below for a letter from the founder, John Hall.

You can still browse legacy old Diamond Scheduler site, tutorials, and FAQs by visiting the legacy site:


A New Chapter for Diamond Scheduler

Dear valued customers and friends,

After 23 years, it’s time for Diamond Scheduler to enter an exciting new chapter.

A new, web-based version of Diamond Scheduler is available now at https://cactusware.com
The web version of Diamond Scheduler contains many of the features and functionalities that you’ve grown accustomed to. It’s fast, fun, and designed to help you achieve your scheduling goals with as little headache as possible. We’ve worked hard over the last 20 months to bring this to life and hope that you check it out for your scheduling needs.

With this, the desktop program will no longer be available for purchase or download, effective November 19th, 2021. I will continue to support active licenses for the desktop program through the duration of the license, as needed.
Additionally, I am stepping back from the company and daily operations will now be handled by my partner, Brett Lindenberg.

Going forward, please send all support inquiries to help@cactusware.com . My inbox will not be monitored for DS support on a regular basis.

I have deeply enjoyed working with the many friends I have gained since 1998. Please take the time to check out the new version of Diamond Scheduler and share your feedback with us so that we can continue to deliver the best experience available in scheduling.

Be well,


Frequently Asked Questions

Do you offer a free trial?

Yes! You can try Diamond Scheduler and only pay if it suits your needs. Note that only partial schedules are shown for free users, but will be unlocked upon upgrading!

Is there a limit on leagues, divisions, teams, etc?

Nope! Create as many as you want. We want you to be successful!

Do you offer tutorials?

Yes! Please visit the tutorials page for video walkthroughs of the application and how-to videos for common tasks.

Can I import my league from the Desktop Client?

Yes! Please visit this page to learn how.

Do you offer support?

Yes. We offer both free and premium support, depending on the issue and your needs. We also offer demos of our product if you need one! Please see the support page for more details.

How can I purchase a license? What types of licenses are available?

Diamond Scheduler is available as an annual subscription. You may cancel your subscription at any time from the billing portal, no contact needed. Billing is done securely through Stripe and you can pay with almost any credit card. We don't store your payment details!

What kind of scheduling constraints are available?

The following constraints are available: minimum days rest, max travel distance from last game or home venue, coach conflicts, venue home teams, max games per day, max games per week, prevention of coach conflicts, max travel

Can I create Practice, Round Robin, and Across-Division schedules?

Yes! Diamond Scheduler supports each of these schedule types in our powerful scheduler.

Does Diamond Scheduler support tournament scheduling?

Yes, we now offer tournament scheduling! Use our tournament bracket generator to create single-elimination or double-elimination brackets for your league.