| 2020 JCYS Members Annual Meeting | Friday, December 11th | Annual JCYS membership meeting to review state of the league and elect 2021 JCYS Board of Directors. Open to all JCYS members. |
| 2021 Spring Baseball & Softball Registration Opens | Monday, January 4th | Registration opens at ossiningjcysll.com |
| Winter Instructional Sessions Begin | TBD | Ossining Recreation Center Gym - Dates & Times TBA. Will be rotated by divisions including Tee Ball, Minors, Intermediate, Little League & Softball |
| In Person Registration | TBD | Ossining Recreation Center |
| Last Day for Discounted Registration | Sunday, February 28th | Registration increases $25 as of March 1st |
| Tee-Ball Coaches Training | TBD | |
| Intermediate, Little League Baseball Assessments | TBD | All Majors/Intermediate (9-10) & Majors/Little League (11-12) eligible players must attend (1) session |
| Majors/Little League Coaches Training | TBD | |
| Intermediate, Little League Baseball Assessments | TBD | All Majors/Intermediate (9-10) & Majors/Little League (11-12) eligible players must attend (1) session |
| All Coaches Meeting / Training | Saturday, March 27th | Please save this date for a 3 hour meeting on safety, skills and coaching resources. |
| Announcement of Rosters & 2021 Schedule | Monday, March 29th | Please save this date for a 3 hour meeting on safety, skills and coaching resources. |
| Intermediate Umpire Training | TBD | Ossining Community Center. Please contact VP, David Capasso at [email protected] if interested! Open to all Little League players age 12 and above.
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| First Day Of On Field Practices | Monday, April 5th |
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| 2021 Opening Day | Saturday, April 10th | |
| Ossining Travel Baseball Tryouts | Saturday, April 17th & Sunday, April 18th | Annual tryouts for Ossining Travel Baseball teams that compete in summer & fall in Greater Hudson Valley Baseball League (GHVBL). Tryouts for 8U, 9U at Veterans Park (Lower Field), tryouts for 11U & 12U at Nelson Park. Dates & Times TBA. |
| Picture Day - All Divisions | Saturday, May 15th | Veterans Park (Majors/Intermediate, Majors/Little League & All Softball) & Roosevelt School Fields (Tee Ball & Minors) |
| Majors/Little League Division Championship Game | Saturday, June 12th | Ryder Park |
| Majors/Intermediate All-Star Game | Saturday, June 19th | Veterans Park (Lower Field) |