| Date/Season | Transaction |
|---|
| 1/21/2023 | Boston Bruins send Nicolas Petan (rental) to the Columbus Blue Jackets for Mason Lohrei, Mason Raymond, BUF 2032 Rnd 3 |
| 12/21/2022 | Columbus Blue Jackets send Luke Kunin to the Pittsburgh Penguins for Mason Raymond |
| 8/21/2021 | Pittsburgh Penguins send Mason Raymond (rental) to the Ottawa Senators for David Farrance, SJS 2027 Rnd 1 |
| 11/25/2020 | Toronto Maple Leafs send Mason Raymond to the Pittsburgh Penguins for Jordan Staal |
| 5/9/2020 | Toronto Maple Leafs send Tyler Biggs to the Pittsburgh Penguins for Mason Raymond |
| 1/28/2019 | New Jersey Devils send Mason Raymond, Nikita Scherbak to the Pittsburgh Penguins for Andre Burakovsky, Jonas Siegenthaler, $4,000,000 |
| 8/9/2017 | Los Angeles Kings send Keith Seabrook, Mason Raymond (rental) to the Nashville Predators for Chris Conner, Denis Grebeshkov, Robby Fabbri |
| 2/15/2012 | Inclusion Draft send Mason Raymond to the Los Angeles Kings for 29th pick |
| 2008 | Drafted in the 3rd round, 71st overall by Edmonton (from NYRangers) |
