| 2020 Spring Registration Opens | Monday, December 16th | Registration is open at www.ossiningjcysll.com |
| In Person Registration | Saturday, January 18th | Ossining Recreation Center 9am-12pm |
| Winter Instructional Sessions Begin | Sunday, February 2nd | Ossining Recreation Center Gym - Dates & Times TBA. Will be rotated by divisions including Tee Ball, Minors, Intermediate, Little League & Softball |
| In Person Registration | Thursday, February 6th | Ossining Recreation Center 6-9pm |
| Softball Pitching Clinic | Sunday, February 23rd | Bear Down Baseball Club - 9:00am-10:30am. Free of charge and open to all players registered for 2020 JCYS spring season. |
| Last Day for Discounted Registration | Saturday, February 29th | Registration increases $25 as of March 1st |
| Tee-Ball Coaches Training | Sunday, March 1st | Bear Down Baseball Club - 9:00am-10:30am |
| Intermediate, Little League, Jr. Softball & Sr. Softball Assessments | Saturday, March 7th | Bear Down Baseball Club - All players in these leagues must attend (1) session. 10:30am-2:00pm |
| Majors/Little League Coaches Training | Sunday, March 8th | Bear Down Baseball Club - 12:45pm - 2:15pm |
| Intermediate, Little League, Jr. Softball & Sr. Softball Assessments | Sunday, March 8th | Bear Down Baseball Club - All players in these leagues must attend (1) session. 2:15pm-6:15pm |
| Minors Coaches Training | Sunday, March 15th | Bear Down Baseball Club - 9:00am-10:30am |
| Finalize Team Rosters & Schedules | Friday, March 20th | All teams to be announced on or before Saturday, March 21st |
| Majors/Intermediate Coaches Training | Sunday, March 22nd | Bear Down Baseball Club - 9:00am-10:30am |
| Intermediate Umpire Training | TBD | Contact VP, David Capasso at [email protected] if interested! Open to all Little League age 12 and above. |
| All Coaches Meeting/Training | Saturday, March 28th | Please save this date for a 3 hour meeting on safety, skills and coaching resources. |
| First Day of On Field Practices | Monday, March 30th | Weather dependent |
| Opening Day Parade | Saturday, April 4th | Tee Ball, Minors, Intermediate, 1st & 2nd Grade Softball & Jr. Softball players and coaches along with Town and Village of Ossining officials to march from Roosevelt School to Veterans Park for on field Opening Day ceremonies. |
| 2020 Opening Day Games | Saturday, April 4th | Schedule TBA |
| Regular Season Games | April 4th - June 20th | |
| Picture Day - LL, Intermediate, Softball | Saturday, April 25th | Veterans Park (Majors/Intermediate & Softball) & Ryder Park (Majors/Little League) |
| Picture Day - T-Ball, Minors | Saturday, May 2nd | Roosevelt School Fields |
| JCYS Board of Directors Meeting | Wednesday, June 3rd | Ossining Recreation Center, 8pm |
| Majors/Little League Division Championship Game | Saturday, June 13th | Ryder Park |
| Majors/Intermediate All-Star Game | Saturday, June 20th | Veterans Park (Lower Field) |