May 31, 2023

• The Vancouver Canucks signed D Jett Woo to a one-year, two-way contract.
• The New York Rangers acquired a 2023 fifth-round draft pick from Edmonton Oilers for C Jayden Grubbe.
• The Carolina Hurricanes signed C Justin Robidas to a three-year, entry-level contract.
• The Edmonton Oilers acquired C Jayden Grubbe from New York Rangers in exchange for a 2023 fifth-round draft pick.

May 28, 2023

• The Buffalo Sabres signed D Ryan Johnson to a two-year, entry-level contract and assigned him to Rochester (AHL).

May 27, 2023

• The Dallas Stars signed D Oskari Laaksonen to a two-year contract.

May 25, 2023

• The Ottawa Senators signed D Nikolas Matinpalo to a one-year, entry-level contract.
• The Buffalo Sabres signed RW Kyl Okposo to a one-year contract and D Vsevolod Komarov to a three-year, entry-level contract.

May 21, 2023

• The New York Islanders signed F Kyle MacLean to a one-year, two-way contract and F Daylan Kuefler to a three-year, entry-level contract.
• The Buffalo Sabres signed D Nikita Novikov to a three-year, entry-level contract.

May 16, 2023

• The Seattle Kraken placed RW Jesper Froden on waivers.

May 10, 2023

• The Tampa Bay Lightning signed G Matt Tomkins to a two-year, two-way contract.
• The Chicago Blackhawks signed G Arvid Soderblom to a two-year contract extension.
• The Boston Bruins signed D Mason Lohrei to a two-year, entry-level contract.

May 9, 2023

• The Tampa Bay Lightning signed C Simon Ryfors to a four-year contract.
• The St. Louis Blues signed RW Mathias Laferriere to a one-year, two-way contract.

May 8, 2023

• The Florida Panthers signed F Mackie Samoskevich to a three-year, entry-level contract.
• The Washington Capitals re-signed F Michael Sgarbossa to a two-year, two-way contract.

May 1, 2023

• The Vancouver Canucks signed RW Jonathan Lekkerimaki to a three-year, entry-level contract.