| May 24, 2019 |
 Edmonton Oilers | Joakim Nygård | Signed to Entry-Level Contract | ✔ |
 Colorado Avalanche | Pavel Francouz | Signed to Standard Contract | |
 Montreal Canadiens | Alex Belzile | Signed to Standard Contract | ✔ |
 Tampa Bay Lightning | Jonne Tammela | Placed on unconditional waivers | |
 Nashville Predators | Filip Pyrochta | Placed on unconditional waivers | |
|
| May 23, 2019 |
 Pittsburgh Penguins | Chad Ruhwedel | Signed to Standard Contract | |
 Winnipeg Jets | Leon Gawanke | Signed to Entry-Level Contract | |
 Chicago Blackhawks | Anton Wedin | Signed to Entry-Level Contract | |
 New York Islanders | Brock Nelson | Signed to Standard Contract | |
|
| May 22, 2019 |
| Edmonton Oilers | Olivier Rodrigue | Signed to Entry-Level Contract | |
|
| May 21, 2019 |
| Edmonton Oilers | Logan Day | Signed to Entry-Level Contract | |
|
| May 20, 2019 |
 Washington Capitals | Brian Pinho | Signed to Standard Contract | |
| Washington Capitals | Shane Gersich | Signed to Standard Contract | |
|
| May 18, 2019 |
| Washington Capitals | Juuso Ikonen | Contract terminated | ✔ |
 Arizona Coyotes | Jens Looke | Contract terminated | ✔ |
| Washington Capitals | Juuso Ikonen | Cleared waivers | |
| Arizona Coyotes | Jens Looke | Cleared waivers | |
|
| May 17, 2019 |
 New York Rangers | Yegor Rykov | Signed to Entry-Level Contract | |
| Washington Capitals | Juuso Ikonen | Placed on unconditional waivers | |
| Arizona Coyotes | Jens Looke | Placed on unconditional waivers | |
 Carolina Hurricanes | Haydn Fleury | Minors  | |
| Carolina Hurricanes | Patrick Brown | Minors | |
| Carolina Hurricanes | Jake Bean | Minors | |
|
| May 16, 2019 |
 Dallas Stars | Esa Lindell | Signed to Standard Contract | |
|
| May 15, 2019 |
| Pittsburgh Penguins | Kasper Björkqvist | Signed to Entry-Level Contract | |
| New York Islanders | Yannick Rathgeb | Contract terminated | ✔ |
| New York Islanders | Yannick Rathgeb | Cleared waivers | |
 Florida Panthers | Aleksi Heponiemi | Signed to Entry-Level Contract | |
 Columbus Blue Jackets | Elvis Merzlikins | Signed to Standard Contract | |
| Carolina Hurricanes | Jake Bean | Emergency Loan  | |
| Carolina Hurricanes | Patrick Brown | Emergency Loan | |
|
| May 14, 2019 |
| Carolina Hurricanes | Jake Bean | Minors | |
| Columbus Blue Jackets | Emil Bemström | Signed to Entry-Level Contract | |
| New York Islanders | Yannick Rathgeb | Placed on unconditional waivers | |
| Carolina Hurricanes | Patrick Brown | Minors | |
|
| May 13, 2019 |
| Colorado Avalanche | Adam Werner | Signed to Entry-Level Contract | |
 Los Angeles Kings | Nikolai Prokhorkin | Signed to Entry-Level Contract | |
| Chicago Blackhawks | Slater Koekkoek | Signed to Standard Contract | |
| Carolina Hurricanes | Jake Bean | Emergency Loan | |
| Carolina Hurricanes | Patrick Brown | Emergency Loan | |
 New Jersey Devils | Mikhail Maltsev | Signed to Entry-Level Contract | |
| New Jersey Devils | Fabian Zetterlund | Signed to Entry-Level Contract | |
|
| May 12, 2019 |
| Carolina Hurricanes | Patrick Brown | Minors | |
| Carolina Hurricanes | Jake Bean | Minors | |
|
| May 10, 2019 |
 Anaheim Ducks | Lukas Dostal | Signed to Entry-Level Contract | |
 Toronto Maple Leafs | Jesper Lindgren | Minors | |
 Calgary Flames | Alexander Yelesin | Signed to Entry-Level Contract | ✔ |
| Carolina Hurricanes | Patrick Brown | Emergency Loan | |
| Carolina Hurricanes | Jake Bean | Emergency Loan | |
 Minnesota Wild | Gerald Mayhew | Signed to Standard Contract | ✔ |
|
