Early in the 2006 season, Ryan got a heavy blow to the face during a shepherd from Byron Pickett, and received a broken cheekbone.

[3] Crowley continued to improve throughout the 2007 season, having gathered 319 disposals in 19 games and earning a regular spot in the Fremantle midfield as a winger/onballer who can kick goals.

In 2008, however, he developed into a defensive midfielder or tagger and notoriously played on opposition stars such as Gary Ablett, Jr. and Daniel Kerr.

He was one of Fremantle's best-performing players in their Grand Final loss to Hawthorn, limiting Sam Mitchell's influence on the game.

[12] In March 2015, it was revealed that Crowley had tested positive for a banned substance after Fremantle's Round 17, 2014 match against Greater Western Sydney.