| Date/Season | Transaction |
|---|
| 4/13/2021 | Pittsburgh Penguins send Evan Fitzpatrick, NYI 2027 Rnd 2 to the Washington Capitals for Roland McKeown |
| 7/26/2018 | Winnipeg Jets send Jason Akeson, Marc-Andre Bergeron, Mikko Lehtonen, Roland McKeown to the Washington Capitals for Graham Knott, Julius Nattinen, Luke Schenn, Vladislav Kamenev, $500,000 |
| 2/23/2017 | Winnipeg Jets send Cameron Gaunce, William Karlsson, WSH 2022 Rnd 3, $485,000 to the Columbus Blue Jackets for Devan Dubnyk, Roland McKeown, Tyler Graovac |
| 2020 | Drafted in the 2nd round, 45th overall by Columbus (from Pittsburgh) |
