York pair Craig Clay and Jamal Fyfield have left the club after agreeing terms over the termination of their contracts.
York boss Nigel Worthington expects new signings Ryan Jarvis and Craig Clay to play keys roles at Bootham Crescent.
Neal Trotman and Danny Whitaker are among seven players released by Chesterfield boss Paul Cook.
Chesterfield will be without Craig Clay for around a month after he was diagnosed with a double hernia.
Scott Boden, Craig Clay and Tendayi Darikwa have agreed new one-year deals with Chesterfield.
Chesterfield midfielders Craig Clay and Tendayi Darikwa have joined non-league side Barrow on a month's loan.
John Sheridan believes midfielder Craig Clay can learn from the experienced heads in the Chesterfield squad.