The Bracket Challenge is a fun and convenient Westchester tennis league

official partner of wilson tennis

Click here to sign up for the Spring Bracket Challenge.
Registrations close on Friday Apr. 12th and the season is played from 4/22 to 6/9.


  • Tennis Channel
  • Forbes
  • The Washington Post
  • Tennis Magazine
  • ESPN Radio

How does the Westchester Bracket Challenge work?

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Convenience

Play 1 match a week with your assigned opponent at a time and location that works for you.

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Local Tournament

Your local Bracket runs for up to 4 weeks and you will play a minimum of 2 matches.

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Fun Competition

Players compete each week in a competitive and friendly atmosphere. All levels welcome!

It’s FREE for PlayYourCourt members or try your first season for ONLY $1

Get ready for your season by joining the Westchester PlayYourCourt community!

Here's what you'll experience as a PYC member

  • Always have someone to practice with

  • Play unlimited practice matches

  • Compete in our Bracket Challenge Flex League

  • Fix what’s broken in your game with quick video tips

  • Get VIP discounted pricing on rackets, balls, shoes & more

  • Get quick answers to tough tennis questions

See what our 35,000+ members are saying...

Frequently Asked Questions

  • How does the Bracket Challenge work?

    Watch this video to see exactly how the Bracket Challenge works.
  • When is the Bracket Challenge?

    The upcoming Late Spring 2024 season runs from April 22nd to June 9th
  • How much does it cost?

    The Bracket Challenge is free to PlayYourCourt members or non-members can try their first season for just $1.
  • How many matches will I play?

    You are guaranteed a minimum of 2 matches. If you lose your first round match you will continue competing in the consolation bracket. Depending on the size of your league, you could play as many as 4 matches if you make it to the finals.
  • When and where are matches played?

    You will play one match a week with your assigned opponent at a time and location that works for you.
  • How do I know my matches will be competitive?

    PlayYourCourt has a proprietary rating system that updates in real time as match scores are reported. If a player has signed up for the wrong division, they will be bumped up or down accordingly.