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The Whole Season, Scheduled in Minutes

Diamond Scheduler turns teams and divisions into a finished season and sends it straight to the platforms leagues already run on. The first schedule takes minutes.

July 27, 2026
The Diamond Scheduler web app's season schedule view
Courtesy of Cactusware

Every San Diego league has that one volunteer. The schedule lands on them in early spring, and with it the field slots, the bye weeks, the doubleheaders, and a spreadsheet that grows meaner by the night. Somebody promised the coaches a finished schedule by opening day, and that somebody is them. Then a roster shifts, a field falls through, and the month of work unravels. One season, one volunteer, one very long month of late-night revisions. Cactusware has been working that exact problem since 1998. Its Diamond Scheduler is sports league scheduling software built for the people who actually run the season, and it exists to do the ugly part for them: turn a league's teams and divisions into a finished schedule and hand the volunteer back their evenings.

What Diamond Scheduler does

Cactusware's Diamond Scheduler builds full-season schedules for baseball, softball, basketball, football, hockey, and soccer leagues. A league's first schedule takes minutes to build. Leagues and divisions are unlimited; a division holds up to 50 teams, and the Elite plan lifts that cap.

The software runs on the web and as a desktop app. The desktop app carries advanced scheduling algorithms.

Tournament brackets included

Bracket play is built into Diamond Scheduler, in single- and double-elimination formats. Round-robin, practice, and playoff schedules are covered too.

Diamond Scheduler's constraint settings cover minimum days rest, max games per day and per week, max travel distance, venue prioritization, doubleheader scheduling, and prevention of coach conflicts.

What Diamond Scheduler plugs into

Diamond Scheduler connects through DirectLink to RAMP Interactive, League Athletics, SportsEngine, Squad Fusion, and TeamSnap. The SportsEngine integration runs in both directions. It pulls league information down from a connected SportsEngine account. Finished schedules go back up to SportsEngine in seconds.

League information loads in by CSV upload. Finished schedules export as CSV files and in Google Calendar, iCal, and Microsoft Outlook formats. A season built in the desktop app moves to the web version in a few clicks, through a JSON export.

Free to try

Trying Diamond Scheduler is free. No credit card is required during the trial. A league pays only if the software suits its needs. Free users see partial schedules until a paid plan unlocks the full ones.

The bottom line

Start the trial, load the real teams and divisions, and judge what comes back on merit.