| Date/Season | Transaction |
|---|
| 1/22/2023 | Vancouver Canucks send VAN 2030 Rnd 3 to the Carolina Hurricanes for Dylan Olsen (rental) |
| 1/21/2023 | Columbus Blue Jackets send Dylan Olsen, $2,000,000, PHI 2029 Rnd 3 to the Carolina Hurricanes for Andy Rogers (rental) |
| 12/27/2022 | Columbus Blue Jackets send Rickard Rakell to the Boston Bruins for Dylan Olsen |
| 12/14/2022 | Buffalo Sabres send Alex Tuch, Nicklas Backstrom, Dylan Olsen to the Boston Bruins for Rich Peverley, Vaclav Karabacek, Colten Teubert, Tim Gettinger, BOS 2032 Rnd 3 |
| 9/14/2022 | Buffalo Sabres send Justin Robidas, Jared Staal, Enver Lisin to the Seattle Kraken for Dylan Olsen |
| 1/16/2021 | Seattle Kraken send Simon Hjalmarsson (rental) to the Calgary Flames for Dylan Olsen |
| 9/23/2020 | San Jose Sharks send Dylan Olsen, Jake Guentzel, Joel Farabee, PIT 2029 Rnd 3 to the Calgary Flames for Jeff Skinner |
| 7/2/2020 | San Jose Sharks send Chris Summer to the Pittsburgh Penguins for Dylan Olsen, PIT 2029 Rnd 3, $800,000 |
| 6/9/2020 | Pittsburgh Penguins send Johan Harju, $500,000 to the Boston Bruins for Dylan Olsen |
| 2/22/2015 | Toronto Maple Leafs send Sebastian Wannstrom to the Florida Panthers for Dylan Olsen |
| 11/29/2010 | Philadelphia Flyers send Dylan Olsen, Jake Gardiner, Jeremy Morin, Kenny Ryan, NAS 2014 Rnd 4, PHI 2014 Rnd 4 to the Florida Panthers for Mikko Lehtonen, Ryan O'Marra, Tomas Kurka |
| 2013 | Drafted in the 1st round, 13rd overall by Anaheim (from Boston) |
