| Registration Opens | January 1 | July 1 |
| Registration Closes | February 19 | August 13 |
| Coaches Meeting | February 22 | August 16 |
| Skills Day | February 26 | August 20 |
| Challenge Baseball Tryouts | February 27 | August 21 |
| Team Drafts | March 3 | August 25 |
| Coaches Clinic | March 5 | August 27 |
| Coaches Team Equipment Pickup | March 5 | August 27 |
| Practices Begin (Baseball & Softball) | March 7 | August 29 |
| Challenge Softball Tryouts | TBD | TBD |
| Practices Begin (Tee Ball) | March 14 | August 29 |
| Labor Day Weekend Break* | -- | September 2-5* |
| Opening Day Games | March 26 | September 17 |
| Spring Break* | April 8-17* | -- |
| Pictures | April 21-27 | September 29 - October 5 |
| All-Star Team Announcements | Between May 15 and June 1 | -- |
| Memorial Day Weekend Break* | May 27-30* | -- |
| End-of-Season Championships | by June 4 | by November 6 |
| All-Stars | > See Tournament Schedules | -- |
* No scheduled league activities during breaks.