| Date/Season | Transaction |
|---|
| 7/4/2021 | Toronto Maple Leafs send Julian Melchiori, TOR 2029 Rnd 3 to the Columbus Blue Jackets for Ryan O'Reilly |
| 8/28/2017 | Montreal Canadiens send Ryan O'Reilly, Sven Andrighetto, MON 2022 Rnd 1, $3,500,000 to the Calgary Flames for Nathan Horton (rental) |
| 2/22/2015 | Winnipeg Jets send Ryan O'Reilly, $1,500,000 to the Montreal Canadiens for Robert Czarnik |
| 8/15/2014 | Winnipeg Jets send Patrice Bergeron, WPG 2022 Rnd 2, WPG 2023 Rnd 2, WPG 2024 Rnd 2 to the Toronto Maple Leafs for Ryan O'Reilly, Future Considerations |
| 3/6/2013 | Toronto Maple Leafs send Luke Schenn, TOR 2017 Rnd 2 to the Edmonton Oilers for Ryan O'Reilly |
| 12/10/2012 | Edmonton Oilers send Ben Lovejoy, Kyle Brodziak, Paul Martin, Taylor Doherty, CAR 2017 Rnd 1, CAR 2017 Rnd 2 to the Anaheim Ducks for Dustin Byfuglien, Ryan O'Reilly |
| 9/26/2010 | Pittsburgh Penguins send Jonathon Merrill, Ryan O'Reilly, $19,000,000 to the Anaheim Ducks for Evgeni Malkin |
| 2013 | Drafted in the 1st round, 29th overall by Pittsburgh (from Columbus) |
