| Registration Opens | January 1 | July 1 |
| Registration Closes | February 13 | August 14 |
| Coaches Meeting | February 16 | August 17 |
| Skills Day | February 20 | August 21 |
| Challenge Baseball Tryouts | February 21 | August 22 |
| Team Drafts | February 25 | August 26 |
| Coaches Clinic | February 27 | August 28 |
| Team Equipment Pickup | February 27 | August 28 |
| Practices Begin (Baseball & Softball) | March 1 | August 30 |
| Challenge Softball Tryouts | March 14 | TBD |
| Practices Begin (Tee Ball) | March 15 | August 30 |
| Labor Day Weekend Break* | -- | September 3-6 |
| Opening Day Games | March 27 | September 18 |
| Spring Break* | April 2-11 | -- |
| Pictures | April 22-28 | September 30 - October 6 |
| All-Star Team Announcements | No earlier than May 15 | -- |
| Memorial Day Weekend Break* | May 28-31 | -- |
| End-of-Season Championships | by June 5 | by November 6 |
| All-Stars | > See Tournament Schedules | -- |
* No scheduled league activities during breaks.