May 29, 2020

• The Chicago Blackhawks agreed to terms with F Matej Chalupa on a two-year contract.

May 15, 2020

• The Washington Capitals extended affiliation agreement with the Hershey Bears through the 2023-24 season.

May 14, 2020

• The Arizona Coyotes announced that the team and President and CEO Ahron Cohen have mutually agreed to part ways.
• The Toronto Maple Leafs signed F Adam Brooks to a two-year contract extension.

May 8, 2020

• The New York Rangers agreed to terms with G Tyler Wall on an entry-level contract.

May 6, 2020

• The Anaheim Ducks signed D Christian Djoos and D Jani Hakanpaa to one-year contract extensions.

May 1, 2020

• The Calgary Flames signed G Dustin Wolf to a three-year entry-level contract.
• The Nashville Predators signed D Ben Harper to a one-year contract.
• The Edmonton Oilers signed D Filip Berglund to a two-year entry-level contract.