| Date/Season | Transaction |
|---|
| 1/14/2020 | Winnipeg Jets send Brendan Gaunce to the Calgary Flames for Kenny Ryan |
| 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 |
| 4/10/2010 | Philadelphia Flyers send Alexander Frolov, Kenny Ryan, Kevin Shattenkirk, TB 2013 Rnd 3 to the Colorado Avalanche for Evgeni Malkin, Jani Hurme, Shaone Morrisonn |
| 2013 | Drafted in the 2nd round, 47th overall by Philly (from Buffalo) |
