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Welcome to the CYB/CYS Website!

Cheshire Youth Baseball and Softball is a non-profit organization whose sole mission is to provide organized, instructional, recreational and competitive baseball and softball programs to Cheshire's youth. It is run entirely by volunteers at the Board of Directors, team manager and coaching levels. League players range from age  6 (T-Ball) through age 19 (American Legion).

The CYB/CYS Board of Directors wish our players and parents every success both on and off the field. We pledge our support as you enter into what we hope is a positive experience; for it is ultimately you, the managers, coaches and parents who will make our program successful and beneficial to Cheshire's youth and Cheshire's future.


Calendar of Events


2020 CYB/CYS Sponsorship

Are you new to the program and want to sponsor your son/ daughters team, then sign up today.  We are still looking and want your business name on the back of their Jersey.


2020 Cheshire Youth Baseball & Softball Sponsorship

The 2020 season was another great one for Cheshire Youth Baseball and Softball! The kids were able to enjoy such a phenomenal season due to the many volunteers who gave their time, and to you, the sponsors willing to support our baseball and softball program. As always, one rule that remains constant is that the kids have fun playing baseball and softball.

That being said, we would once again like to ask that you consider sponsoring a team for Cheshire Youth Baseball and Softball. The league relies on our great sponsors to keep registration fees low and invest in our fields.

A Team Sponsorship is $350 which inlcudes a company name on back of shirt and a link to your website from ours as well as promotion opportunities. 

To sponsor a team, you may complete this On-line Link;  Click Here: 2020 Sponsorship Link

Or complete this form and mail a check in:

https://s3.amazonaws.com/files.leagueathletics.com/Images/Club/16257/2020 Sponsor letter copy.pdf

by posted 01/25/2020
Last Day - Register today and pay late.

Register Today and pay later - please don't delay as we have evaluations this weekend and want all those interested in playing to attend.  Please see below for details.


2020 Spring Baseball Registrationis NOW OPEN!


Note Time Change for evaluations.

All evals to be Held at DBat in Cheshire. (613 West Johnson Ave, Cheshire, CT)

Minors and Major Evals  - (Coaches need to be in attendance)

Saturday 2/29 12pm - 3pm

  • Minors: 12pm - 2pm
  • Majors: 1pm - 3pm

AAA and Minors and Major Makeup Evals - (Coaches need to be in attendance)

Saturday 3/7 12pm - 3pm

  • AAA: 12pm - 2pm
  • Makeup: 1pm - 2pm


Registration Deadlines for:

  • T-Ball (A) & AA - 03/07/2020
  • AAA, Minors & Majors - 03/01/2020

$25 Late fee will be applied to all registrations after deadlines have passed.


Note: Babe Ruth Registration NOW OPEN!!! (visit CYBCYS.org for more info)


Note: Umpire Registration is NOW OPEN!!!!! (visit home page CYBCYS.org for more info)


The season will begin (weather and fields permitting) on March 30th for practices.  Regular season play for AA, AAA, Minors and Majors will begin on April 27th and run through June 13th.  Playoffs will be held during the week of June 14th.  Most teams will have two games a week with one being during the week and one on Saturday.  Practices and Games during the week will start after 5:30pm and last approx. 2hrs.  Weekend games will start at 9am and also last approx. 2hrs.


Coaching - if you are interested in coaching, Manager or assistant, please email Jeff Sutherland @ cybcysvpbase@gmail.com or me @ cybcyspres@gmail.com.  


We will be holding evaluations for AAA, Minors and Majors.  The evaluations will be held at D-Bat in Cheshire on Saturday 2/29 & Saturday 3/7.  Anyone who is planning to Coach a team must be available to assist during the evaluations.  Specific Details to come out closer to dates listed below.


Levels of Play: Click on links to Register


  • T-Ball (A) - ages 5 - 6.    http://assn.la/Reg/?r=1:278375
    • The T-Ball (A) Division The players in this age group will participate in an indoor clinic for the first 4 weeks and then go outside to begin games.  At this level we are committed to teach the fundamentals of baseball while having fun.   


  • AA - ages 6 -7.    http://assn.la/Reg/?r=1:278384
    • The AA Division is typically for the 2nd year player, ages 6-7. Games are played with 4 outfielders, modified stealing rules and a combination Coach/Player Pitch format.  


  • ​AAAages 7 - 8.    http://assn.la/Reg/?r=1:278797
    • The AAA Division is typically for the 3rd-4th year player, ages 7-8. Games are played with 4 outfielders, modified stealing rules and a combination Coach/Player Pitch format.  


  • Minors - ages 9 -10.    http://assn.la/Reg/?r=1:278799
    • The Minors Division is 100% player pitch, stealing permitted once ball crosses plate


  • Majors - ages 11 - 12.    http://assn.la/Reg/?r=1:278802
    • The Majors Division is 100% player pitch, stealing permitted once ball crosses plate

by posted 01/15/2020
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