| Date/Season | Transaction |
|---|
| 6/8/2021 | Riverview Royals send S4 MON 2 to the South Esk Scotsmen for Jamie Benn, S6 SOU 1 |
| 5/17/2021 | Riverview Royals send Ryan Johansen, Jamie Benn to the South Esk Scotsmen for Jonathan Toews, Clayton Keller, Boone Jenner |
| 4/9/2021 | Riverview Royals send Nicklas Backstrom to the Moncton Melons for Jamie Benn, S4 MON 2 |
| 4/8/2021 | Saint John Kings send Sidney Crosby, Jamie Benn, Alex Pietrangelo, Ryan McDonagh, Gemel Smith, Kyle Okposo to the Moncton Melons for Mika Zibanejad, Evander Kane, Dustin Byfuglien, Torey Krug, S4 MON 1 |
| 3/19/2021 | Saint John Kings send John Tavares, Jaden Schwartz, John Carlson, Blake Wheeler, Damon Severson to the Albert County Renegade for Sidney Crosby, Mitchell Marner, Ryan McDonagh, Jamie Benn, Justin Braun |
| 1 | Drafted in the 5 round, 47 overall by ALB |
